PL217415B1 - Podstawione 4-aminocykloheksanole, środek leczniczy zawierający podstawiony 4-aminocykloheksanol, zastosowanie podstawionego 4-aminocykloheksanolu oraz sposoby wytwarzania podstawionych 4-aminocykloheksanoli - Google Patents
Podstawione 4-aminocykloheksanole, środek leczniczy zawierający podstawiony 4-aminocykloheksanol, zastosowanie podstawionego 4-aminocykloheksanolu oraz sposoby wytwarzania podstawionych 4-aminocykloheksanoliInfo
- Publication number
- PL217415B1 PL217415B1 PL372307A PL37230703A PL217415B1 PL 217415 B1 PL217415 B1 PL 217415B1 PL 372307 A PL372307 A PL 372307A PL 37230703 A PL37230703 A PL 37230703A PL 217415 B1 PL217415 B1 PL 217415B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- substituted
- unsubstituted
- dimethylamine
- alkyl
- Prior art date
Links
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical class NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000003814 drug Substances 0.000 claims abstract description 19
- 208000002193 Pain Diseases 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 230000036407 pain Effects 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- -1 4-substituted 4-aminocyclohexanone Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 26
- 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 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002524 organometallic group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- GLBNOVDCIAHFGY-UHFFFAOYSA-N 4-[(2-fluorophenyl)methoxy]-n,n-dimethyl-1-phenylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1OCC1=CC=CC=C1F GLBNOVDCIAHFGY-UHFFFAOYSA-N 0.000 claims description 6
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- OIVVTCNNLXFJKW-UHFFFAOYSA-N 1-benzyl-4-[(2-fluorophenyl)methoxy]-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(OCC=2C(=CC=CC=2)F)CCC1(N(C)C)CC1=CC=CC=C1 OIVVTCNNLXFJKW-UHFFFAOYSA-N 0.000 claims description 4
- HPVSPFRUSNSKMG-UHFFFAOYSA-N 1-benzyl-4-[(3-fluorophenyl)methoxy]-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(OCC=2C=C(F)C=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 HPVSPFRUSNSKMG-UHFFFAOYSA-N 0.000 claims description 4
- FIMOYFCIKAMGOA-UHFFFAOYSA-N 1-benzyl-4-[(4-fluorophenyl)methoxy]-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(OCC=2C=CC(F)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 FIMOYFCIKAMGOA-UHFFFAOYSA-N 0.000 claims description 4
- DQKMHUOIXVYFRT-UHFFFAOYSA-N 4-[(3-fluorophenyl)methoxy]-n,n-dimethyl-1-phenylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1OCC1=CC=CC(F)=C1 DQKMHUOIXVYFRT-UHFFFAOYSA-N 0.000 claims description 4
- HDTDYEQDEYDXTG-UHFFFAOYSA-N 4-[(4-fluorophenyl)methoxy]-n,n-dimethyl-1-phenylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1OCC1=CC=C(F)C=C1 HDTDYEQDEYDXTG-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- UCGMDNNGRIWRPN-UHFFFAOYSA-N n,n-dimethyl-1-phenyl-4-phenylmethoxycyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1OCC1=CC=CC=C1 UCGMDNNGRIWRPN-UHFFFAOYSA-N 0.000 claims description 4
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- UGLITRCNFYADQS-UHFFFAOYSA-N 1-benzyl-n,n-dimethyl-4-phenylmethoxycyclohexan-1-amine Chemical compound C1CC(OCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 UGLITRCNFYADQS-UHFFFAOYSA-N 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 125000001979 organolithium group Chemical group 0.000 claims description 3
- FTCXWNUJMSGUKP-UHFFFAOYSA-N 1-amino-4-oxocyclohexane-1-carbonitrile Chemical class N#CC1(N)CCC(=O)CC1 FTCXWNUJMSGUKP-UHFFFAOYSA-N 0.000 claims description 2
- PVBLJPCMWKGTOH-UHFFFAOYSA-N 1-aminocyclohexan-1-ol Chemical class NC1(O)CCCCC1 PVBLJPCMWKGTOH-UHFFFAOYSA-N 0.000 claims description 2
- BXBJZYXQHHPVGO-UHFFFAOYSA-N 4-hydroxycyclohexan-1-one Chemical class OC1CCC(=O)CC1 BXBJZYXQHHPVGO-UHFFFAOYSA-N 0.000 claims description 2
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- 230000001154 acute effect Effects 0.000 claims description 2
- 208000005298 acute pain Diseases 0.000 claims description 2
- 125000005219 aminonitrile group Chemical group 0.000 claims description 2
- 150000001499 aryl bromides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000002981 neuropathic effect Effects 0.000 claims description 2
- 229940079593 drug Drugs 0.000 abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 18
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
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- OMFAXTHGUKJURS-UHFFFAOYSA-N 4-(dimethylamino)-4-phenylcyclohexan-1-ol Chemical compound C=1C=CC=CC=1C1(N(C)C)CCC(O)CC1 OMFAXTHGUKJURS-UHFFFAOYSA-N 0.000 description 6
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10213051A DE10213051B4 (de) | 2002-03-23 | 2002-03-23 | Substituierte 4-Aminocyclohexanole |
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| Publication Number | Publication Date |
|---|---|
| PL372307A1 PL372307A1 (en) | 2005-07-11 |
| PL217415B1 true PL217415B1 (pl) | 2014-07-31 |
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| PL372307A PL217415B1 (pl) | 2002-03-23 | 2003-03-18 | Podstawione 4-aminocykloheksanole, środek leczniczy zawierający podstawiony 4-aminocykloheksanol, zastosowanie podstawionego 4-aminocykloheksanolu oraz sposoby wytwarzania podstawionych 4-aminocykloheksanoli |
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| MXPA06013270A (es) | 2004-05-14 | 2007-04-23 | Johnson & Johnson | Compuestos de opioide carboxamido. |
| EP1966126A1 (de) * | 2005-12-22 | 2008-09-10 | Basf Se | Verfahren zur herstellung von zyklischen o-alkylierten aminoalkoholen |
| DE102005061428A1 (de) * | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
| US20090215725A1 (en) * | 2008-02-26 | 2009-08-27 | Grunenthal Gmbh | Substituted 4-aminocyclohexane derivatives |
| 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 |
| EP2260022B1 (de) | 2008-03-27 | 2017-01-04 | Grünenthal GmbH | Substituierte cyclohexyldiamine |
| AU2009228637B2 (en) | 2008-03-27 | 2013-12-19 | Grunenthal Gmbh | (Hetero-)aryl cyclohexane derivatives |
| HRP20140650T1 (hr) * | 2008-03-27 | 2014-09-26 | Grünenthal GmbH | Hidroksimetilcikloheksilamini |
| KR20120075500A (ko) | 2008-03-27 | 2012-07-06 | 그뤼넨탈 게엠베하 | 치환된 4-아미노사이클로헥산 유도체 |
| 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. |
| KR101999937B1 (ko) | 2010-12-22 | 2019-07-12 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 시스-1-암모늄-4-알콕시시클로헥산카보니트릴 염의 제조 방법 |
| WO2025243298A1 (en) | 2024-05-22 | 2025-11-27 | Adama Makhteshim Ltd. | Novel substituted aminocyclohexanecarbonitriles |
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| US3975436A (en) * | 1974-03-27 | 1976-08-17 | American Home Products Corporation | Benzylamine narcotic antagonists |
| US3937818A (en) * | 1974-03-27 | 1976-02-10 | American Home Products Corporation | Benzylamine narcotic antagonists |
| US4366172A (en) | 1977-09-29 | 1982-12-28 | The Upjohn Company | 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use |
| US4143158A (en) * | 1978-03-24 | 1979-03-06 | American Home Products Corporation | Inhibition of prolactin release by an opiate antagonist |
| US4446065A (en) * | 1981-12-22 | 1984-05-01 | Syva Company | Phencyclidine compounds and assays for its determination |
| ES2104142T3 (es) * | 1992-03-26 | 1997-10-01 | Univ British Columbia | Aminociclohexilamidas para utilizacion antirritmica y anestesica. |
| DE69429524T2 (de) * | 1993-09-24 | 2002-08-08 | The University Of British Columbia, Vancouver | Aminocyclohexylester und ihre anwendung |
| GB9406043D0 (en) * | 1994-03-26 | 1994-05-18 | Smithkline Beecham Plc | Compounds |
| WO1996014307A1 (en) | 1994-11-07 | 1996-05-17 | Pfizer Inc. | Certain substituted benzylamine derivatives; a new class of neuropeptide y1 specific ligands |
| MX9708597A (es) * | 1995-05-09 | 1998-02-28 | Bayer Ag | Cetoenoles alquil-dihalogenofenil substituidos como pesticidas y herbicidas. |
| US5808146A (en) * | 1995-11-09 | 1998-09-15 | Emory University | Amino acid analogs for tumor imaging |
| DE19547766A1 (de) * | 1995-12-20 | 1997-06-26 | Gruenenthal Gmbh | 1-Phenyl-2-dimethylaminomethyl-cyclohexan-1-ol-verbindungen als pharmazeutische Wirkstoffe |
| WO1997036868A1 (de) * | 1996-04-02 | 1997-10-09 | Bayer Aktiengesellschaft | Substituierte phenylketoenole als schädlingsbekämpfungsmittel und herbizide |
| DK1277749T3 (da) * | 1996-08-05 | 2007-01-29 | Bayer Cropscience Ag | 2- og 2,5-substituerede phenylketoenoler |
| CN1217918C (zh) * | 1998-04-01 | 2005-09-07 | 卡迪欧梅制药公司 | 氨基环己基醚化合物和其用途 |
| DE19818732A1 (de) * | 1998-04-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| DE19915602A1 (de) * | 1999-04-07 | 2000-10-19 | Gruenenthal Gmbh | 3-Amino-4-arylpropan-1-ol-Derivate, deren Herstellung und Verwendung |
| DE19915601A1 (de) * | 1999-04-07 | 2000-10-19 | Gruenenthal Gmbh | 3-Amino-3-arylpropan-1-ol-Derivate, deren Herstellung und Verwendung |
| DE10016544A1 (de) * | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
| GB0012214D0 (en) * | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| DE10032587A1 (de) * | 2000-07-05 | 2002-01-17 | Bayer Ag | 4-Alkoxy-cyclohexan-1-amino-carbonsäureester und Verfahren zu ihrer Herstellung |
| CA2424600C (en) * | 2000-10-06 | 2008-12-02 | Tanabe Seiyaku Co., Ltd. | Aliphatic nitrogenous five-membered ring compounds |
| JP4329290B2 (ja) * | 2000-10-06 | 2009-09-09 | 田辺三菱製薬株式会社 | 脂肪族含窒素五員環化合物 |
-
2002
- 2002-03-23 DE DE10213051A patent/DE10213051B4/de not_active Expired - Fee Related
-
2003
- 2003-03-18 CA CA2480038A patent/CA2480038C/en not_active Expired - Fee Related
- 2003-03-18 EP EP03708253A patent/EP1487778B1/de not_active Expired - Lifetime
- 2003-03-18 JP JP2003578315A patent/JP4663239B2/ja not_active Expired - Fee Related
- 2003-03-18 DK DK03708253.4T patent/DK1487778T3/da active
- 2003-03-18 PT PT03708253T patent/PT1487778E/pt unknown
- 2003-03-18 SI SI200332177T patent/SI1487778T1/sl unknown
- 2003-03-18 ES ES03708253T patent/ES2387983T3/es not_active Expired - Lifetime
- 2003-03-18 WO PCT/EP2003/002812 patent/WO2003080557A1/de not_active Ceased
- 2003-03-18 AU AU2003212366A patent/AU2003212366A1/en not_active Abandoned
- 2003-03-18 PL PL372307A patent/PL217415B1/pl unknown
- 2003-03-21 PE PE2003000286A patent/PE20040162A1/es not_active Application Discontinuation
- 2003-03-24 AR ARP030101014A patent/AR039115A1/es unknown
-
2004
- 2004-09-23 US US10/947,551 patent/US7211694B2/en not_active Expired - Fee Related
-
2012
- 2012-09-13 CY CY20121100835T patent/CY1113116T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7211694B2 (en) | 2007-05-01 |
| DE10213051B4 (de) | 2013-03-07 |
| AU2003212366A1 (en) | 2003-10-08 |
| US20050187220A1 (en) | 2005-08-25 |
| CA2480038C (en) | 2010-10-12 |
| DE10213051A1 (de) | 2003-10-30 |
| JP2005526795A (ja) | 2005-09-08 |
| CA2480038A1 (en) | 2003-10-02 |
| SI1487778T1 (sl) | 2012-09-28 |
| EP1487778B1 (de) | 2012-07-11 |
| EP1487778A1 (de) | 2004-12-22 |
| WO2003080557A1 (de) | 2003-10-02 |
| DK1487778T3 (da) | 2012-08-06 |
| ES2387983T3 (es) | 2012-10-05 |
| JP4663239B2 (ja) | 2011-04-06 |
| PT1487778E (pt) | 2012-07-26 |
| PE20040162A1 (es) | 2004-03-22 |
| CY1113116T1 (el) | 2016-04-13 |
| PL372307A1 (en) | 2005-07-11 |
| AR039115A1 (es) | 2005-02-09 |
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