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 (de) | 2002-11-11 | 2003-11-05 | Spirocyclische cyclohexan-derivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20052761L NO20052761L (no) | 2005-06-07 |
| NO20052761D0 NO20052761D0 (no) | 2005-06-07 |
| NO331818B1 true NO331818B1 (no) | 2012-04-10 |
Family
ID=32185555
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. |
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| EP (4) | EP2233487B1 (es) |
| JP (4) | JP4728645B2 (es) |
| KR (2) | KR101075817B1 (es) |
| CN (2) | CN101693714B (es) |
| AR (2) | AR041932A1 (es) |
| AT (1) | ATE441650T1 (es) |
| AU (2) | AU2003296563B2 (es) |
| BR (2) | BRPI0318811B8 (es) |
| CA (1) | CA2505555C (es) |
| CO (1) | CO5580765A2 (es) |
| CY (2) | CY1110558T1 (es) |
| DE (2) | DE10252667A1 (es) |
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| EC (1) | ECSP055786A (es) |
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| HK (3) | HK1080478A1 (es) |
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| PT (2) | PT1560835E (es) |
| RU (1) | RU2354656C2 (es) |
| SI (2) | SI1560835T1 (es) |
| WO (1) | WO2004043967A1 (es) |
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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 |
| DE102005005446A1 (de) * | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE102004032051A1 (de) | 2004-07-01 | 2006-01-19 | 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 |
| PT1842533E (pt) * | 2003-08-06 | 2013-05-17 | Gruenenthal Gmbh | Forma de dosagem protegida contra abuso |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| DE102004020220A1 (de) * | 2004-04-22 | 2005-11-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE10360792A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10360793A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102004032103A1 (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 |
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| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| WO2007062175A2 (en) * | 2005-11-21 | 2007-05-31 | Amgen Inc. | Spiro-substituted tricyclic heterocycles cxcr3 antagonists |
| DE102006019597A1 (de) * | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102006033109A1 (de) | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| DE102006033114A1 (de) * | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| DE102006046745A1 (de) * | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
| DE102007009235A1 (de) * | 2007-02-22 | 2008-09-18 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009319A1 (de) * | 2007-02-22 | 2008-08-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007011485A1 (de) | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
| TWI454288B (zh) | 2008-01-25 | 2014-10-01 | Gruenenthal Chemie | 藥物劑型 |
| PE20091823A1 (es) | 2008-03-27 | 2009-12-10 | Gruenenthal Chemie | Ciclohexildiaminas sustituidas |
| ES2482108T3 (es) | 2008-03-27 | 2014-08-01 | Grünenthal GmbH | Hidroximetilciclohexilaminas |
| CL2009000731A1 (es) * | 2008-03-27 | 2009-05-15 | Gruenenthal Gmbh | Compuestos derivados de ciclohexano espirociclicos sustituidos, composicion farmaceutica que contiene a dicho compuesto y su uso como moduladores del receptor de opioides µ y el receptor orl-1 para tratar el dolor, ansiedad, depresion, epilepsia, alzheimer, abuso de alcohol, hipertension, anorexia, obesidad y diarrea. |
| WO2009118169A1 (de) * | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | Spiro(5.5)undecan derivate |
| AU2009228637B2 (en) | 2008-03-27 | 2013-12-19 | Grunenthal Gmbh | (Hetero-)aryl cyclohexane derivatives |
| EP2502907B1 (de) | 2008-03-27 | 2018-08-29 | Grünenthal GmbH | Substituierte 4-Aminocyclohexan-Derivate |
| PT2273983T (pt) | 2008-05-09 | 2016-10-28 | Gruenenthal Gmbh | Processo para a preparação de uma formulação em pó intermediária e uma forma de dosagem sólida final sob utilização de uma etapa de congelamento por atomização |
| ES2560210T3 (es) * | 2009-07-22 | 2016-02-17 | Grünenthal GmbH | Forma de dosificación resistente a la manipulación para opiádes sensibles a la oxidación |
| CN102573805A (zh) | 2009-07-22 | 2012-07-11 | 格吕伦塔尔有限公司 | 热熔挤出的控制释放剂型 |
| RU2641648C1 (ru) * | 2009-12-04 | 2018-01-19 | Суновион Фармасьютикалз, Инк. | Полициклические соединения и способы их применения |
| 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 |
| MX354686B (es) | 2010-08-04 | 2018-03-15 | Gruenenthal Gmbh Star | Forma de dosificacion farmaceutica que comprende 6'-fluoro-(n-metil- o n,n-dimetil-)-4-fenil-4'.9'-dihidro-3'h-espi ro[ciclohexan-1,1'-pirano[3,4,b]indol]-4-amina para el tratamiento de dolor neuropatico. |
| NZ604662A (en) * | 2010-08-04 | 2014-08-29 | Gruenenthal Gmbh | Pharmaceutical dosage form comprising 6’-fluoro-(n-methyl- or n,n-dimethyl-)-4-phenyl-4’,9’-dihydro-3’h-spiro[cyclohexane-1,1’-pyrano[3,4,b]indol]-4-amine |
| RU2589831C2 (ru) * | 2010-08-04 | 2016-07-10 | Грюненталь Гмбх | ЛЕКАРСТВЕННАЯ ДОЗИРОВАННАЯ ФОРМА, КОТОРАЯ СОДЕРЖИТ 6'-ФТОР-(N-МЕТИЛ- ИЛИ N, N-ДИМЕТИЛ-)-4-ФЕНИЛ-4', 9'-ДИГИДРО-3'Н-СПИРО[ЦИКЛОГЕКСАН-1, 1'-ПИРАНО[3, 4, b]ИНДОЛ]-4-АМИН |
| PT2600839T (pt) * | 2010-08-04 | 2018-04-17 | Gruenenthal Gmbh | Forma farmacêutica compreendendo 6'-fluoro-(n-metil- ou n,n-dimetil-)-4-fenil-4',9'-di-hidro-3'h-espiro[ciclo-hexano-1,1'-pirano[3,4,b]indol]-4-amina |
| NZ607479A (en) | 2010-09-02 | 2015-06-26 | Gruenenthal Chemie | Tamper resistant dosage form comprising an anionic polymer |
| RU2604676C2 (ru) | 2010-09-02 | 2016-12-10 | Грюненталь Гмбх | Устойчивая к разрушению лекарственная форма, содержащая неорганическую соль |
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