HRP20171773T1 - Kristalični oblik od (s)-(2-(6-kloro-7-metil-1h-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2h-1,2,3-triazol-2-il)fenil)metanona i njegova uporaba kao antagonisti receptora oreksina - Google Patents
Kristalični oblik od (s)-(2-(6-kloro-7-metil-1h-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2h-1,2,3-triazol-2-il)fenil)metanona i njegova uporaba kao antagonisti receptora oreksina Download PDFInfo
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- HRP20171773T1 HRP20171773T1 HRP20171773TT HRP20171773T HRP20171773T1 HR P20171773 T1 HRP20171773 T1 HR P20171773T1 HR P20171773T T HRP20171773T T HR P20171773TT HR P20171773 T HRP20171773 T HR P20171773T HR P20171773 T1 HRP20171773 T1 HR P20171773T1
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- NBGABHGMJVIVBW-QHCPKHFHSA-N [(2s)-2-(5-chloro-4-methyl-1h-benzimidazol-2-yl)-2-methylpyrrolidin-1-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound N1([C@](CCC1)(C)C=1NC2=CC=C(Cl)C(C)=C2N=1)C(=O)C1=CC(OC)=CC=C1N1N=CC=N1 NBGABHGMJVIVBW-QHCPKHFHSA-N 0.000 title claims 18
- 229940123730 Orexin receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 20
- 238000000634 powder X-ray diffraction Methods 0.000 claims 10
- 238000010586 diagram Methods 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 230000005855 radiation Effects 0.000 claims 4
- 208000019116 sleep disease Diseases 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 238000002156 mixing Methods 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 230000006806 disease prevention Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 206010013980 Dyssomnias Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000006199 Parasomnias Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000011067 equilibration Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
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- 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
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- 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
- A61P25/20—Hypnotics; Sedatives
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- 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
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- 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
- A61P25/24—Antidepressants
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Claims (16)
1. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona, naznačen time, da:
• pokazuje vršne vrijednosti u difrakcijskom dijagramu praha X-zraka, uz sljedeće refrakcijske kutove 2θ: 8,6°, 15,2° i 21,3°; ili
• pokazuje vršne vrijednosti u difrakcijskom dijagramu praha X-zraka, uz sljedeće refrakcijske kutove 2θ: 13,4°, 18,3° i 24,0°.
2. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema zahtjevu 1, naznačen time, da pokazuje vršne vrijednosti u difrakcijskom dijagramu praha X-zraka, uz sljedeće refrakcijske kutove 2θ: 8,6°, 15,2°, i 21,3°, gdje se navedeni dijagram difrakcije praha X-zraka dobiva pomoću kombinirane radijacije Cu Kα1 i Cu Kα2, bez Kα2-strippinga; a preciznost za 2θ-vrijednosti leži u rasponu od 2θ +/- 0,2°.
3. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema zahtjevu 1, naznačen time, da pokazuje vršne vrijednosti u difrakcijskom dijagramu praha X-zraka, uz sljedeće refrakcijske kutove 2θ: 8,6°, 11,5°, 13,4°, 14,6°, 15,2°, 15,5°, 19,3°, 21,3°, 22,4°, i 26,4°, gdje se navedeni dijagram difrakcije praha X-zraka dobiva pomoću kombinirane radijacije Cu Kα1 i Cu Kα2, bez Kα2-strippinga; a preciznost za 2θ-vrijednosti leži u rasponu od 2θ +/- 0,2°.
4. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema zahtjevima 2 ili 3, naznačen time, da u biti pokazuje uzorak difrakcije praha X-zraka kao što je prikazano na Slici 2.
5. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 2 do 4, naznačen time, da navedeni kristalični oblik je polu-hidrat.
6. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 2 do 5, naznačen time, da se dobiva pomoću sljedećeg:
a) miješanje 2 g SPOJA kao amorfnog materijala s 8 mL smjese etanol/voda u omjeru 1/4 (volumen/volumen);
b) dodavanje oko 0,05 g kristalnih zrnaca SPOJA u kristaličnom obliku 1;
c) protresanje uz brzinu od 300 rpm u trajanju oko 16 sati na sobnoj temperaturi;
d) filtriranje i ispiranje čvrste grude s 2 mL smjese etanol/voda u omjeru 1/4 (v/v) i sušenje proizvoda na sobnoj temperaturi i uz smanjeni tlak od oko 10 mbara u trajanju od 4 sata; i
e) otvoreno ekvilibriranje na sobnoj temperaturi i uz oko 60% relativne vlažnosti u trajanju od 2 sata.
7. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema zahtjevu 1, naznačen time, da pokazuje vršne vrijednosti u difrakcijskom dijagramu praha X-zraka, uz sljedeće refrakcijske kutove 2θ: 13,4°, 18,3°, i 24,0°, gdje se navedeni dijagram difrakcije praha X-zraka dobiva pomoću kombinirane radijacije Cu Kα1 i Cu Kα2, bez Kα2-strippinga; a preciznost za 2θ-vrijednosti leži u rasponu od 2θ +/- 0,2°.
8. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema zahtjevu 1, naznačen time, da pokazuje vršne vrijednosti u difrakcijskom dijagramu praha X-zraka, uz sljedeće refrakcijske kutove 2θ: 10,9°, 13,4°, 14,3°, 14,9°, 18,3°, 20,9°, 21,1°, 21,8°, 24,0°, i 30,1°, gdje se navedeni dijagram difrakcije praha X-zraka dobiva pomoću kombinirane radijacije Cu Kα1 i Cu Kα2, bez Kα2-strippinga; a preciznost za 2θ-vrijednosti leži u rasponu od 2θ +/- 0,2°.
9. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema zahtjevima 7 ili 8, naznačen time, da u biti pokazuje uzorak difrakcije praha X-zraka kao što je prikazano na Slici 3.
10. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 7 do 9, naznačen time, da navedeni kristalični oblik je anhidrat.
11. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 7 do 10, naznačen time, da se dobiva pomoću sljedećeg:
a) miješanje 10 mg SPOJA u kristaličnom obliku 1 u 0,05 mL acetonitrila;
b) miješanje u zatvorenoj fijali od 4 mL u trajanju do tri dana;
c) izolacija; i sušenje uz smanjeni tlak na sobnoj temperaturi u trajanju od 2 sata.
12. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 1 do 11, naznačen time, da se upotrebljava kao lijek.
13. Farmaceutski sastav, naznačen time, da kao djelotvorni sastojak obuhvaća kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 1 do 11, i najmanje jedan farmaceutski prikladan nosač.
14. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 1 do 11, naznačen time, da se upotrebljava u proizvodnji farmaceutskog sastava, pri čemu navedeni farmaceutski sastav, kao djelotvorni sastojak obuhvaća spoj (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona, i najmanje jedan farmaceutski prikladan materijal za nosač.
15. Kristalični oblik spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 1 do 11, ili farmaceutski sastav prema zahtjevu 13, naznačen time, da se upotrebljava u liječenju ili prevenciji bolesti ili poremećaja odabranih iz skupine koju čine: poremećaji spavanja odabrani iz skupine koja se sastoji od disomnija, parasomnija, poremećaja spavanja povezanih s općim medicinskim stanjem i poremećaja spavanja izazvanih supstancama; poremećaj anksioznosti; i poremećaj ovisnosti.
16. Uporaba kristaličnog oblika spoja (S)-(2-(6-kloro-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2H-1,2,3-triazol-2-il)fenil)metanona prema bilo kojem od zahtjeva 1 do 11, naznačena time, da je za proizvodnju lijeka za liječenje ili prevenciju bolesti ili poremećaja odabranih iz skupine koju čine: poremećaji spavanja, poremećaji anksioznosti, poremećaji ovisnosti, kognitivne disfunkcije, poremećaji raspoloženja, i poremećaji teka.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2013060596 | 2013-12-03 | ||
| PCT/IB2014/066508 WO2015083070A1 (en) | 2013-12-03 | 2014-12-02 | Crystalline form of (s)-(2-(6-chloro-7-methyl-1h-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1 -yl)(5-methoxy-2-(2h-1,2,3-triazol-2-yl)phenyl)methanone and its use as orexin receptor antagonists |
| EP14824107.8A EP3077389B1 (en) | 2013-12-03 | 2014-12-02 | Crystalline form of (s)-(2-(6-chloro-7-methyl-1h-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1-yl)(5-methoxy-2-(2h-1,2,3-triazol-2-yl)phenyl)methanone and its use as orexin receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171773T1 true HRP20171773T1 (hr) | 2017-12-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171773TT HRP20171773T1 (hr) | 2013-12-03 | 2017-11-16 | Kristalični oblik od (s)-(2-(6-kloro-7-metil-1h-benzo[d]imidazol-2-il)-2-metilpirolidin-1-il)(5-metoksi-2-(2h-1,2,3-triazol-2-il)fenil)metanona i njegova uporaba kao antagonisti receptora oreksina |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US9914720B2 (hr) |
| EP (1) | EP3077389B1 (hr) |
| JP (1) | JP6496733B2 (hr) |
| KR (1) | KR102361418B1 (hr) |
| CN (1) | CN105793257B (hr) |
| AU (1) | AU2014358742B2 (hr) |
| CA (1) | CA2929423C (hr) |
| CL (1) | CL2016001342A1 (hr) |
| CY (1) | CY1119695T1 (hr) |
| DK (1) | DK3077389T3 (hr) |
| EA (1) | EA030137B1 (hr) |
| ES (1) | ES2651475T3 (hr) |
| HK (1) | HK1225731B (hr) |
| HR (1) | HRP20171773T1 (hr) |
| HU (1) | HUE035731T2 (hr) |
| IL (1) | IL245923B (hr) |
| LT (1) | LT3077389T (hr) |
| MA (1) | MA39163B1 (hr) |
| MX (1) | MX364208B (hr) |
| MY (1) | MY179862A (hr) |
| NO (1) | NO3077389T3 (hr) |
| NZ (1) | NZ721438A (hr) |
| PH (1) | PH12016500988A1 (hr) |
| PL (1) | PL3077389T3 (hr) |
| PT (1) | PT3077389T (hr) |
| SA (1) | SA516371231B1 (hr) |
| SI (1) | SI3077389T1 (hr) |
| TW (1) | TWI664177B (hr) |
| UA (1) | UA119549C2 (hr) |
| WO (1) | WO2015083070A1 (hr) |
| ZA (1) | ZA201604499B (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ703448A (en) | 2012-06-04 | 2017-07-28 | Actelion Pharmaceuticals Ltd | Benzimidazole-proline derivatives |
| 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 |
| AU2014358766B2 (en) | 2013-12-04 | 2019-01-17 | Idorsia Pharmaceuticals Ltd | Use of benzimidazole-proline derivatives |
| MX2019012902A (es) * | 2017-05-03 | 2019-12-16 | Idorsia Pharmaceuticals Ltd | Preparacion de derivados de acido 2-([1,2,3]triazol-2-il)-benzoico . |
| BR112022020924A2 (pt) | 2020-04-19 | 2023-02-14 | Idorsia Pharmaceuticals Ltd | Métodos de tratamento de um transtorno do sono, a sonolência diurna em um indivíduo, a insônia, e, daridorexante na forma de sal livre ou farmaceuticamente aceitável |
| US20240300925A1 (en) * | 2021-02-02 | 2024-09-12 | Medshine Discovery Inc. | Tetrahydropyrrolocyclic compound and application thereof |
| CN115925699B (zh) * | 2022-02-25 | 2023-10-03 | 南京知和医药科技有限公司 | 具有镇痛活性的稠环化合物及其制备方法与用途 |
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| US3282927A (en) | 1964-05-21 | 1966-11-01 | Bristol Myers Co | 5-phenyl-4-thiazolylpenicillins |
| PT1289955E (pt) | 2000-06-16 | 2005-08-31 | Smithkline Beecham Plc | Piperidinas para utilizacao como antagonistas dos receptores da orexina |
| WO2002028839A1 (en) | 2000-10-06 | 2002-04-11 | Neurogen Corporation | Benzimidazole and indole derivatives as crf receptor modulators |
| EP1353918B1 (en) | 2000-11-28 | 2005-01-12 | Smithkline Beecham Plc | Morpholine derivatives as antagonists of orexin receptors |
| US20040192673A1 (en) | 2001-05-05 | 2004-09-30 | Pascale Gaillard | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| US7432270B2 (en) | 2001-05-05 | 2008-10-07 | Smithkline Beecham P.L.C. | N-aroyl cyclic amines |
| EP1399441B1 (en) * | 2001-06-28 | 2006-07-05 | Smithkline Beecham Plc | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| GB0115862D0 (en) | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| GB0124463D0 (en) | 2001-10-11 | 2001-12-05 | Smithkline Beecham Plc | Compounds |
| GB0127145D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Compounds |
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