JP2005526795A5 - - Google Patents
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- Publication number
- JP2005526795A5 JP2005526795A5 JP2003578315A JP2003578315A JP2005526795A5 JP 2005526795 A5 JP2005526795 A5 JP 2005526795A5 JP 2003578315 A JP2003578315 A JP 2003578315A JP 2003578315 A JP2003578315 A JP 2003578315A JP 2005526795 A5 JP2005526795 A5 JP 2005526795A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- substituted
- dimethylamine
- compound
- unsubstituted
- 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.)
- Granted
Links
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 19
- -1 1H-indol-3-yl-acetoxy Chemical group 0.000 claims 13
- 125000006239 protecting group Chemical group 0.000 claims 13
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical class NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 150000007530 organic bases Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- MPEIIIWBVXISKP-UHFFFAOYSA-N 4-aminohexan-1-ol Chemical class CCC(N)CCCO MPEIIIWBVXISKP-UHFFFAOYSA-N 0.000 claims 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- 239000007818 Grignard reagent Substances 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 150000001347 alkyl bromides Chemical group 0.000 claims 2
- 230000003444 anaesthetic effect Effects 0.000 claims 2
- 125000005418 aryl aryl group Chemical group 0.000 claims 2
- 150000001499 aryl bromides Chemical class 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 claims 2
- 150000004795 grignard reagents Chemical class 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 125000001979 organolithium group Chemical group 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- FTCXWNUJMSGUKP-UHFFFAOYSA-N 1-amino-4-oxocyclohexane-1-carbonitrile Chemical class N#CC1(N)CCC(=O)CC1 FTCXWNUJMSGUKP-UHFFFAOYSA-N 0.000 claims 1
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical class OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 claims 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010011878 Deafness Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000018526 Narcotic-Related disease Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 244000061458 Solanum melongena Species 0.000 claims 1
- 235000002597 Solanum melongena Nutrition 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 208000009205 Tinnitus Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 150000001262 acyl bromides Chemical group 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 125000005219 aminonitrile group Chemical group 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 235000009120 camo Nutrition 0.000 claims 1
- 235000005607 chanvre indien Nutrition 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000029142 excretion Effects 0.000 claims 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 claims 1
- 229960003132 halothane Drugs 0.000 claims 1
- 230000010370 hearing loss Effects 0.000 claims 1
- 231100000888 hearing loss Toxicity 0.000 claims 1
- 208000016354 hearing loss disease Diseases 0.000 claims 1
- 239000011487 hemp Substances 0.000 claims 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 claims 1
- 229960002456 hexobarbital Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 230000001777 nootropic effect Effects 0.000 claims 1
- 201000005040 opiate dependence Diseases 0.000 claims 1
- 239000000014 opioid analgesic Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 231100000886 tinnitus Toxicity 0.000 claims 1
- 0 **C(CC1)(CCC1(OS*)OI)N(*)* Chemical compound **C(CC1)(CCC1(OS*)OI)N(*)* 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10213051A DE10213051B4 (de) | 2002-03-23 | 2002-03-23 | Substituierte 4-Aminocyclohexanole |
| PCT/EP2003/002812 WO2003080557A1 (de) | 2002-03-23 | 2003-03-18 | Substituierte 4-aminocyclohexanole |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005526795A JP2005526795A (ja) | 2005-09-08 |
| JP2005526795A5 true JP2005526795A5 (https=) | 2010-08-26 |
| JP4663239B2 JP4663239B2 (ja) | 2011-04-06 |
Family
ID=28050784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003578315A Expired - Fee Related JP4663239B2 (ja) | 2002-03-23 | 2003-03-18 | 置換された４−アミノシクロヘキサノール |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7211694B2 (https=) |
| EP (1) | EP1487778B1 (https=) |
| JP (1) | JP4663239B2 (https=) |
| AR (1) | AR039115A1 (https=) |
| AU (1) | AU2003212366A1 (https=) |
| CA (1) | CA2480038C (https=) |
| CY (1) | CY1113116T1 (https=) |
| DE (1) | DE10213051B4 (https=) |
| DK (1) | DK1487778T3 (https=) |
| ES (1) | ES2387983T3 (https=) |
| PE (1) | PE20040162A1 (https=) |
| PL (1) | PL217415B1 (https=) |
| PT (1) | PT1487778E (https=) |
| SI (1) | SI1487778T1 (https=) |
| WO (1) | WO2003080557A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005245403B2 (en) | 2004-05-14 | 2012-04-19 | Janssen Pharmaceutica N.V. | Carboxamido opioid compounds |
| DE102005061428A1 (de) * | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
| CN101341116A (zh) * | 2005-12-22 | 2009-01-07 | 巴斯夫欧洲公司 | 制备o-烷基化环状氨基醇的方法 |
| US20090215725A1 (en) * | 2008-02-26 | 2009-08-27 | Grunenthal Gmbh | Substituted 4-aminocyclohexane derivatives |
| AU2009228647B2 (en) | 2008-03-27 | 2013-07-04 | Grunenthal Gmbh | Substituted spirocyclic cyclohexane derivatives |
| JP5529843B2 (ja) | 2008-03-27 | 2014-06-25 | 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 | 置換シクロヘキシルジアミン |
| EP2280941B1 (de) | 2008-03-27 | 2015-05-06 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| ES2375543T3 (es) | 2008-03-27 | 2012-03-01 | Grünenthal GmbH | Derivados de espiro(5.5)undecano. |
| ES2464102T3 (es) | 2008-03-27 | 2014-05-30 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| CN102046591B (zh) * | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
| 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 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3937818A (en) * | 1974-03-27 | 1976-02-10 | American Home Products Corporation | Benzylamine narcotic antagonists |
| US3975436A (en) * | 1974-03-27 | 1976-08-17 | 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 |
| JP3190676B2 (ja) * | 1992-03-26 | 2001-07-23 | ザ ユニバーシティー オブ ブリティッシュ コロンビア | アミノシクロヘキシルアミド類を含有する抗不整脈及び麻酔剤 |
| 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 |
| CN1131209C (zh) * | 1995-05-09 | 2003-12-17 | 拜尔公司 | 可用作杀虫剂和除草剂的烷基－二卤代苯基取代的酮烯醇 |
| 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 |
| CN1215390A (zh) * | 1996-04-02 | 1999-04-28 | 拜尔公司 | 取代的苯基酮烯醇杀虫剂及除草剂 |
| ES2275796T3 (es) * | 1996-08-05 | 2007-06-16 | Bayer Cropscience Ag | Fenilcetoenoles 2- y 2,5-substituidos. |
| CA2326777C (en) * | 1998-04-01 | 2011-12-20 | Nortran Pharmaceuticals Inc. | Aminocyclohexyl ether compounds and uses thereof |
| 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 |
| 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 |
| US7138397B2 (en) * | 2000-10-06 | 2006-11-21 | Tanabe Seiyaku Co., Ltd. | Nitrogenous 5-membered ring compounds |
-
2002
- 2002-03-23 DE DE10213051A patent/DE10213051B4/de not_active Expired - Fee Related
-
2003
- 2003-03-18 ES ES03708253T patent/ES2387983T3/es not_active Expired - Lifetime
- 2003-03-18 JP JP2003578315A patent/JP4663239B2/ja not_active Expired - Fee Related
- 2003-03-18 WO PCT/EP2003/002812 patent/WO2003080557A1/de not_active Ceased
- 2003-03-18 PL PL372307A patent/PL217415B1/pl unknown
- 2003-03-18 DK DK03708253.4T patent/DK1487778T3/da active
- 2003-03-18 PT PT03708253T patent/PT1487778E/pt unknown
- 2003-03-18 EP EP03708253A patent/EP1487778B1/de not_active Expired - Lifetime
- 2003-03-18 CA CA2480038A patent/CA2480038C/en not_active Expired - Fee Related
- 2003-03-18 SI SI200332177T patent/SI1487778T1/sl unknown
- 2003-03-18 AU AU2003212366A patent/AU2003212366A1/en not_active Abandoned
- 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
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