CA2699504C - Tetrahydroquinoline derivatives for treating post-traumatic stress disorders - Google Patents
Tetrahydroquinoline derivatives for treating post-traumatic stress disorders Download PDFInfo
- Publication number
- CA2699504C CA2699504C CA2699504A CA2699504A CA2699504C CA 2699504 C CA2699504 C CA 2699504C CA 2699504 A CA2699504 A CA 2699504A CA 2699504 A CA2699504 A CA 2699504A CA 2699504 C CA2699504 C CA 2699504C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- pharmaceutically acceptable
- phenyl
- compound
- alkyl
- 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.)
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- 208000028173 post-traumatic stress disease Diseases 0.000 title claims abstract description 19
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000003814 drug Substances 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims description 41
- -1 2-(4-trifluoromethyl-phenyl)-ethyl Chemical group 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- BYGBTDRDPBJUBB-LHIMUUITSA-N (2r)-2-[(1s)-6,7-dimethoxy-1-[2-[4-(trifluoromethyl)phenyl]ethyl]-3,4-dihydro-1h-isoquinolin-2-yl]-n-methyl-2-phenylacetamide;hydrochloride Chemical compound Cl.C([C@H]1C2=CC(OC)=C(OC)C=C2CCN1[C@@H](C(=O)NC)C=1C=CC=CC=1)CC1=CC=C(C(F)(F)F)C=C1 BYGBTDRDPBJUBB-LHIMUUITSA-N 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 3
- DKMACHNQISHMDN-RPLLCQBOSA-N Almorexant Chemical group C([C@H]1C2=CC(OC)=C(OC)C=C2CCN1[C@@H](C(=O)NC)C=1C=CC=CC=1)CC1=CC=C(C(F)(F)F)C=C1 DKMACHNQISHMDN-RPLLCQBOSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 description 20
- 238000000034 method Methods 0.000 description 13
- 241000700159 Rattus Species 0.000 description 12
- 208000019901 Anxiety disease Diseases 0.000 description 11
- 230000036506 anxiety Effects 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 229940123730 Orexin receptor antagonist Drugs 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 230000024188 startle response Effects 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229960003529 diazepam Drugs 0.000 description 4
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 230000002996 emotional effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 208000011688 Generalised anxiety disease Diseases 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 208000029364 generalized anxiety disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- DKMACHNQISHMDN-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-[2-[4-(trifluoromethyl)phenyl]ethyl]-3,4-dihydro-1h-isoquinolin-2-yl]-n-methyl-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)NC)N1CCC2=CC(OC)=C(OC)C=C2C1CCC1=CC=C(C(F)(F)F)C=C1 DKMACHNQISHMDN-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 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 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 208000027534 Emotional disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 108050000742 Orexin Receptor Proteins 0.000 description 1
- 102000008834 Orexin receptor Human genes 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Chemical group 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229940000041 nervous system drug Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2007054130 | 2007-10-10 | ||
| IBPCT/IB2007/054130 | 2007-10-10 | ||
| PCT/IB2008/054138 WO2009047723A2 (en) | 2007-10-10 | 2008-10-09 | Tetrahydroquinoline derivatives for treating post-traumatic stress disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2699504A1 CA2699504A1 (en) | 2009-04-16 |
| CA2699504C true CA2699504C (en) | 2015-11-24 |
Family
ID=40467356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2699504A Active CA2699504C (en) | 2007-10-10 | 2008-10-09 | Tetrahydroquinoline derivatives for treating post-traumatic stress disorders |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US9532985B2 (enExample) |
| EP (1) | EP2207550B1 (enExample) |
| JP (1) | JP5883222B2 (enExample) |
| KR (1) | KR101733247B1 (enExample) |
| CN (1) | CN101820878B (enExample) |
| AR (1) | AR068768A1 (enExample) |
| AU (1) | AU2008309194B2 (enExample) |
| BR (1) | BRPI0818617A2 (enExample) |
| CA (1) | CA2699504C (enExample) |
| CY (1) | CY1114799T1 (enExample) |
| DK (1) | DK2207550T3 (enExample) |
| EA (1) | EA017443B1 (enExample) |
| ES (1) | ES2444418T3 (enExample) |
| HR (1) | HRP20140214T1 (enExample) |
| IL (1) | IL204838A (enExample) |
| MA (1) | MA31800B1 (enExample) |
| MX (1) | MX2010003711A (enExample) |
| MY (1) | MY153044A (enExample) |
| NZ (1) | NZ585086A (enExample) |
| PE (1) | PE20091010A1 (enExample) |
| PL (1) | PL2207550T3 (enExample) |
| PT (1) | PT2207550E (enExample) |
| SI (1) | SI2207550T1 (enExample) |
| TW (1) | TWI428129B (enExample) |
| UA (1) | UA99150C2 (enExample) |
| WO (1) | WO2009047723A2 (enExample) |
| ZA (1) | ZA201003251B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010513466A (ja) | 2006-12-22 | 2010-04-30 | アクテリオン ファーマシューティカルズ リミテッド | ５，６，７，８−テトラヒドロ−イミダゾ［１，５−ａ］ピラジン誘導体 |
| US20110105514A1 (en) | 2008-06-25 | 2011-05-05 | Hamed Aissaoui | 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine compounds |
| EP2402322A1 (en) | 2010-07-02 | 2012-01-04 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-tetrahydroisoquinoline derivative and its use as orexin receptor antagonist |
| KR101802726B1 (ko) | 2010-08-24 | 2017-11-29 | 액테리온 파마슈티칼 리미티드 | 오렉신 수용체 안타고니스트로서의 프롤린 술폰아미드 유도체 |
| SI2626350T1 (sl) | 2010-09-22 | 2015-09-30 | Eisai R&D Management Co., Ltd. | Spojina ciklopropana |
| WO2012063207A1 (en) | 2010-11-10 | 2012-05-18 | Actelion Pharmaceuticals Ltd | Lactam derivatives useful as orexin receptor antagonists |
| WO2012085852A1 (en) | 2010-12-22 | 2012-06-28 | Actelion Pharmaceuticals Ltd | 3,8-diaza-bicyclo[4.2.0]oct-8-yl amides |
| KR101873083B1 (ko) | 2011-02-18 | 2018-06-29 | 이도르시아 파마슈티컬스 리미티드 | 오렉신 길항제로서 유용한 신규 피라졸 및 이미다졸 유도체 |
| WO2012114252A1 (en) | 2011-02-21 | 2012-08-30 | Actelion Pharmaceuticals Ltd | Novel indole and pyrrolopyridine amides |
| WO2013050938A1 (en) | 2011-10-04 | 2013-04-11 | Actelion Pharmaceuticals Ltd | 3,7-diazabicyclo[3.3.1]nonane and 9-oxa-3,7-diazabicyclo[3.3.1]nonane derivatives |
| DK2776430T3 (en) | 2011-11-08 | 2016-05-09 | Actelion Pharmaceuticals Ltd | 2- (1,2,3-triazol-2-yl) benzamide and 3- (1,2,3-triazol-2-yl) PICOLINAMIDDERIVATER AS orexin receptor antagonists |
| PL2855453T3 (pl) | 2012-06-04 | 2017-05-31 | Actelion Pharmaceuticals Ltd. | Pochodne benzimidazoloproliny |
| JP6244365B2 (ja) | 2012-10-10 | 2017-12-06 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | ［オルトビ−（ヘテロ−）アリール］−［２−（メタビ−（ヘテロ−）アリール）−ピロリジン−１−イル］−メタノン誘導体であるオレキシン受容体アンタゴニスト |
| EP2970241A1 (en) | 2013-03-12 | 2016-01-20 | Actelion Pharmaceuticals Ltd. | Azetidine amide derivatives as orexin receptor antagonists |
| EA030137B1 (ru) | 2013-12-03 | 2018-06-29 | Идорсиа Фармасьютиклз Лтд | Кристаллическая форма (s)-(2-(6-хлор-7-метил-1н-бензо[d]имидазол-2-ил)-2-метилпирролидин-1-ил)(5-метокси-2-(2h-1,2,3-триазол-2-ил)фенил)метанона и ее применение в качестве антагонистов орексинового рецептора |
| UA119151C2 (uk) | 2013-12-03 | 2019-05-10 | Ідорсія Фармасьютікалз Лтд | КРИСТАЛІЧНА СОЛЬОВА ФОРМА (S)-(2-(6-ХЛОР-7-МЕТИЛ-1H-БЕНЗО[d]ІМІДАЗОЛ-2-ІЛ)-2-МЕТИЛПІРОЛІДИН-1-ІЛ)(5-МЕТОКСИ-2-(2H-1,2,3-ТРИАЗОЛ-2-ІЛ)ФЕНІЛ)МЕТАНОНУ ЯК АНТАГОНІСТ ОРЕКСИНОВОГО РЕЦЕПТОРА |
| LT3077391T (lt) | 2013-12-04 | 2018-10-25 | Idorsia Pharmaceuticals Ltd | Benzimidazolo prolino darinių panaudojimas |
| JP6659681B2 (ja) | 2014-10-23 | 2020-03-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 不眠症を治療するための組成物および方法 |
| JP7179049B2 (ja) * | 2017-08-01 | 2022-11-28 | ベルゲン ファーマシューティカル、 エルエルシー | オレキシン受容体拮抗薬の結晶形及びその製造方法並びに用途 |
| WO2020007964A1 (en) | 2018-07-05 | 2020-01-09 | Idorsia Pharmaceuticals Ltd | 2-(2-azabicyclo[3.1.0]hexan-1-yl)-1h-benzimidazole derivatives |
| WO2020007977A1 (en) | 2018-07-06 | 2020-01-09 | Idorsia Pharmaceuticals Ltd | 7-trifluoromethyl-[1,4]diazepan derivatives |
| WO2020099511A1 (en) | 2018-11-14 | 2020-05-22 | Idorsia Pharmaceuticals Ltd | Benzimidazole-2-methyl-morpholine derivatives |
| AR129309A1 (es) | 2022-05-13 | 2024-08-07 | Idorsia Pharmaceuticals Ltd | Derivados de hidrazina-n-carboxamida cíclica sustituida con tiazoloaril-metilo |
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|---|---|---|---|---|
| MXPA02008797A (es) | 2000-03-14 | 2005-09-08 | Actelion Pharmaceuticals Ltd | Derivados de 1,2,3,4-tetrahidroisoquinolina. |
| CA2518945A1 (en) * | 2003-03-26 | 2004-10-07 | Actelion Pharmaceuticals Ltd. | Tetrahydroisoquinolyl acetamide derivatives for use as orexin receptor antagonists |
| WO2005118548A1 (en) * | 2004-03-01 | 2005-12-15 | Actelion Pharmaceuticals Ltd | Substituted 1,2,3,4-tetrahydroisoquinoline derivatives |
| US7501395B2 (en) * | 2005-04-25 | 2009-03-10 | Eisai R & D Management Co., Ltd. | Method of screening for antianxiety drugs |
| AU2007226203A1 (en) * | 2006-03-15 | 2007-09-20 | Actelion Pharmaceuticals Ltd | Tetrahydroisoquinoline derivatives to enhance memory function |
| EP2402322A1 (en) | 2010-07-02 | 2012-01-04 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-tetrahydroisoquinoline derivative and its use as orexin receptor antagonist |
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