JP2015522606A5 - - Google Patents
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- Publication number
- JP2015522606A5 JP2015522606A5 JP2015522234A JP2015522234A JP2015522606A5 JP 2015522606 A5 JP2015522606 A5 JP 2015522606A5 JP 2015522234 A JP2015522234 A JP 2015522234A JP 2015522234 A JP2015522234 A JP 2015522234A JP 2015522606 A5 JP2015522606 A5 JP 2015522606A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- compound
- formula
- piperidin
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
- -1 C 1 to 6 -haloalkoxy Chemical group 0.000 claims description 23
- 150000001721 carbon Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- BVUJMFFRMZRNAT-UHFFFAOYSA-N [1-(1-methyl-6-oxopyridazin-3-yl)piperidin-4-yl] 4-cyclobutylpiperazine-1-carboxylate Chemical compound C1=CC(=O)N(C)N=C1N1CCC(OC(=O)N2CCN(CC2)C2CCC2)CC1 BVUJMFFRMZRNAT-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 102000004384 Histamine H3 receptors Human genes 0.000 claims description 5
- 108090000981 Histamine H3 receptors Proteins 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- AKBDWSBBADJJLP-UHFFFAOYSA-N [1-(6-oxo-1h-pyridazin-3-yl)piperidin-4-yl] 4-cyclobutylpiperazine-1-carboxylate Chemical compound C1CN(C2CCC2)CCN1C(=O)OC(CC1)CCN1C=1C=CC(=O)NN=1 AKBDWSBBADJJLP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940116351 sebacate Drugs 0.000 claims description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 206010041349 Somnolence Diseases 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010040981 Sleep attacks Diseases 0.000 claims 2
- 208000032140 Sleepiness Diseases 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 230000037007 arousal Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- TYQXTWOOOKDKPO-UHFFFAOYSA-N piperidin-4-yl 4-propan-2-ylpiperazine-1-carboxylate Chemical compound C1CN(C(C)C)CCN1C(=O)OC1CCNCC1 TYQXTWOOOKDKPO-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 239000012296 anti-solvent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012078933 | 2012-07-20 | ||
| CNPCT/CN2012/078933 | 2012-07-20 | ||
| CN2013078309 | 2013-06-28 | ||
| CNPCT/CN2013/078309 | 2013-06-28 | ||
| PCT/IB2013/055916 WO2014013469A1 (en) | 2012-07-20 | 2013-07-18 | Carbamate/urea derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015522606A JP2015522606A (ja) | 2015-08-06 |
| JP2015522606A5 true JP2015522606A5 (https=) | 2015-10-08 |
| JP6203841B2 JP6203841B2 (ja) | 2017-09-27 |
Family
ID=49263333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015522234A Expired - Fee Related JP6203841B2 (ja) | 2012-07-20 | 2013-07-18 | カルバメート／尿素誘導体 |
Country Status (41)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201321353A (zh) | 2011-10-08 | 2013-06-01 | Novartis Ag | 胺基甲酸酯／尿素衍生物 |
| US9034874B2 (en) | 2012-07-20 | 2015-05-19 | Novartis Ag | Carbamate/urea derivatives |
| EP3391886A1 (en) | 2017-04-19 | 2018-10-24 | Novartis AG | The use of a h3r inverse agonist for the treatment of shift work disorder |
| US20190381056A1 (en) | 2018-06-17 | 2019-12-19 | Axsome Therapeutics, Inc. | Compositions for delivery of reboxetine |
| US20210379062A1 (en) | 2018-10-11 | 2021-12-09 | Novartis Ag | The use of a H3R inverse agonist for the treatment of excessive daytime sleepiness associated with parkinson's disease (PD) |
| US11020402B2 (en) | 2018-10-15 | 2021-06-01 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
| US20200147093A1 (en) | 2018-10-15 | 2020-05-14 | Axsome Therapeutics, Inc. | Use of esreboxetine to treat nervous system disorders such as fibromyalgia |
| WO2022113008A1 (en) | 2020-11-27 | 2022-06-02 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
| US12565478B1 (en) | 2025-01-21 | 2026-03-03 | Axsome Therapeutics, Inc. | (S)-2-((S)-(2-ethoxyphenoxy)(phenyl)methyl)-4-nitrosomorpholine |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2567518B1 (fr) | 1984-07-11 | 1987-11-13 | Sanofi Sa | Nouveaux composes a noyau heterocyclique azote, leur preparation et les medicaments qui en contiennent |
| TW301607B (https=) | 1993-03-09 | 1997-04-01 | Takeda Pharm Industry Co Ltd | |
| IL150650A0 (en) | 2000-01-20 | 2003-02-12 | Eisai Co Ltd | Piperidine derivatives and pharmaceutical compositions containing the same |
| EP1373251A2 (en) | 2001-03-13 | 2004-01-02 | Schering Corporation | Non-imidazole compounds as histamine h3 antagonists |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| PL1615909T3 (pl) | 2003-04-23 | 2009-01-30 | Glaxo Group Ltd | Pochodne piperazyny i ich zastosowanie w leczeniu chorób neurologicznych i psychicznych |
| UA83416C2 (en) | 2004-02-13 | 2008-07-10 | Баниу Фармасьютикал Ко., Лтд. | Fused ring 4-oxopyrimidine derivative |
| SE0401971D0 (sv) | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Piperidne derivatives |
| EP1706401A1 (en) | 2004-09-02 | 2006-10-04 | Teva Pharmaceutical Industries Ltd. | Preparation of olmesartan medoxomil |
| KR20090102883A (ko) | 2004-09-02 | 2009-09-30 | 테바 파마슈티컬 인더스트리즈 리미티드 | 올메살탄 메독소밀의 정제 |
| US7851474B2 (en) | 2005-08-02 | 2010-12-14 | Neurogen Corporation | Dipiperazinyl ketones and related analogues |
| WO2007052124A1 (en) | 2005-11-04 | 2007-05-10 | Pfizer Limited | Tetrahydronaphthyridine derivative |
| WO2007063934A1 (ja) | 2005-12-02 | 2007-06-07 | Mitsubishi Tanabe Pharma Corporation | 脂環式複素環化合物 |
| CN102015668A (zh) * | 2007-12-05 | 2011-04-13 | 阿斯利康(瑞典)有限公司 | 用作瘦蛋白受体调节剂的哌嗪衍生物及其用途 |
| TWI498115B (zh) * | 2007-12-27 | 2015-09-01 | Daiichi Sankyo Co Ltd | 咪唑羰基化合物 |
| WO2009142732A2 (en) | 2008-05-20 | 2009-11-26 | Cephalon, Inc. | Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands |
| EP2527340B1 (en) | 2010-01-22 | 2016-08-17 | Taiho Pharmaceutical Co., Ltd. | Piperazine compound having a pgds inhibitory effect |
| TW201217312A (en) * | 2010-09-22 | 2012-05-01 | Gruenenthal Gmbh | Substituted benzamide compounds |
| TW201321353A (zh) * | 2011-10-08 | 2013-06-01 | Novartis Ag | 胺基甲酸酯／尿素衍生物 |
| US9034874B2 (en) | 2012-07-20 | 2015-05-19 | Novartis Ag | Carbamate/urea derivatives |
-
2013
- 2013-07-17 US US13/944,354 patent/US9034874B2/en active Active
- 2013-07-18 JP JP2015522234A patent/JP6203841B2/ja not_active Expired - Fee Related
- 2013-07-18 WO PCT/IB2013/055916 patent/WO2014013469A1/en not_active Ceased
- 2013-07-18 AU AU2013291617A patent/AU2013291617B2/en not_active Ceased
- 2013-07-18 LT LTEP13770709.7T patent/LT2875016T/lt unknown
- 2013-07-18 DK DK13770709.7T patent/DK2875016T3/da active
- 2013-07-18 RS RS20171048A patent/RS56479B1/sr unknown
- 2013-07-18 SG SG10201700188PA patent/SG10201700188PA/en unknown
- 2013-07-18 SG SG11201408020RA patent/SG11201408020RA/en unknown
- 2013-07-18 AP AP2014008109A patent/AP3710A/en active
- 2013-07-18 CU CUP2015000006A patent/CU24248B1/es unknown
- 2013-07-18 SI SI201330787T patent/SI2875016T1/sl unknown
- 2013-07-18 PT PT137707097T patent/PT2875016T/pt unknown
- 2013-07-18 CA CA2878006A patent/CA2878006C/en active Active
- 2013-07-18 NO NO13770709A patent/NO2875016T3/no unknown
- 2013-07-18 HR HRP20171692TT patent/HRP20171692T1/hr unknown
- 2013-07-18 KR KR1020157001045A patent/KR102150739B1/ko not_active Expired - Fee Related
- 2013-07-18 NZ NZ702346A patent/NZ702346A/en not_active IP Right Cessation
- 2013-07-18 EA EA201590250A patent/EA026091B1/ru not_active IP Right Cessation
- 2013-07-18 CN CN201380038422.1A patent/CN104470911B/zh not_active Expired - Fee Related
- 2013-07-18 HU HUE13770709A patent/HUE035592T2/en unknown
- 2013-07-18 MX MX2015000903A patent/MX362059B/es active IP Right Grant
- 2013-07-18 PL PL13770709T patent/PL2875016T3/pl unknown
- 2013-07-18 ES ES13770709.7T patent/ES2648512T3/es active Active
- 2013-07-18 MY MYPI2014003308A patent/MY168752A/en unknown
- 2013-07-18 BR BR112015001207-8A patent/BR112015001207B1/pt not_active IP Right Cessation
- 2013-07-18 IN IN10449DEN2014 patent/IN2014DN10449A/en unknown
- 2013-07-18 PE PE2015000045A patent/PE20151155A1/es active IP Right Grant
- 2013-07-18 EP EP13770709.7A patent/EP2875016B1/en active Active
- 2013-07-19 UY UY0001034921A patent/UY34921A/es unknown
- 2013-07-19 TW TW102125975A patent/TWI597276B/zh not_active IP Right Cessation
- 2013-07-21 JO JOP/2013/0218A patent/JO3439B1/ar active
- 2013-07-22 AR ARP130102583A patent/AR092354A1/es active IP Right Grant
-
2014
- 2014-11-27 ZA ZA2014/08805A patent/ZA201408805B/en unknown
- 2014-11-28 TN TN2014000497A patent/TN2014000497A1/fr unknown
- 2014-12-05 PH PH12014502743A patent/PH12014502743A1/en unknown
-
2015
- 2015-01-09 CL CL2015000056A patent/CL2015000056A1/es unknown
- 2015-01-11 IL IL236656A patent/IL236656A/en active IP Right Grant
- 2015-01-20 CR CR20150019A patent/CR20150019A/es unknown
- 2015-01-20 CO CO15009915A patent/CO7170173A2/es unknown
- 2015-01-20 GT GT201500012A patent/GT201500012A/es unknown
- 2015-04-14 US US14/685,926 patent/US9273026B2/en active Active
-
2016
- 2016-02-22 US US15/049,739 patent/US9624192B2/en active Active
-
2017
- 2017-03-07 US US15/452,430 patent/US20170275264A1/en not_active Abandoned
- 2017-10-25 CY CY20171101112T patent/CY1119492T1/el unknown
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