HRP20150371T1 - Supstituirani derivati 1,2,3,4-tetrahidroizokinolina - Google Patents
Supstituirani derivati 1,2,3,4-tetrahidroizokinolina Download PDFInfo
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- HRP20150371T1 HRP20150371T1 HRP20150371TT HRP20150371T HRP20150371T1 HR P20150371 T1 HRP20150371 T1 HR P20150371T1 HR P20150371T T HRP20150371T T HR P20150371TT HR P20150371 T HRP20150371 T HR P20150371T HR P20150371 T1 HRP20150371 T1 HR P20150371T1
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- Prior art keywords
- acid
- phenyl
- sleep
- compound according
- disorders
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- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 4
- 208000019116 sleep disease Diseases 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 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 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000020685 sleep-wake disease Diseases 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010022437 insomnia Diseases 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 230000033764 rhythmic process Effects 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 208000032140 Sleepiness Diseases 0.000 claims 1
- 206010041349 Somnolence Diseases 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010118 dystonia Diseases 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000003818 metabolic dysfunction Effects 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 230000037321 sleepiness Effects 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Pharmacology & Pharmacy (AREA)
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Claims (11)
1. Spoj, naznačen time, daje to (2R)-2-{(S)-6,7-dimetoksi-1-[2-(4-trifluorometil-fenil)-etil]-3,4-dihidro-1H-izokinolin-2-il}-N-metil-2-fenil-acetamid:
[image]
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1, naznačen time, da je to (2R)-2-{(S)-6,7-dimetoksi-1-[2-(4-trifluorometil-fenil)-etil]-3,4-dihidro-1H-izokinolin-2-il}-N-metil-2-fenil-aeetamid u obliku slobodne lužine.
3. Spoj prema zahtjevu 1, naznačen time, da je to (2R)-2-{(S)-6,7-dimetoksi-1-[2-(4-trifluorometil-fenil)-etil]-3,4-dihidro-1H-izokinolin-2-il}-N-metil-2-fenil-acetamid u obliku farmaceutski prihvatljive soli adicijske kiseline;
pri čemu je kisela komponenta od navedene farmaceutski prihvatljive soli odabrana iz skupine koju čine klorovodična kiselina, bromovodična kiselina, jodovodična kiselina, sumporna kiselina, fosforna kiselina, dušična kiselina, limunska kiselina, mravlja kiselina, octena kiselina, maleična kiselina, vinska kiselina, fumarna kiselina, benzoeva kiselina, pamoična kiselina, stearinska kiselina, metansulfonska kiselina, p-toluensulfonska kiselina, salicilna kiselina, sukcinska kiselina i trifluoroctena kiselina.
4. Spoj prema zahtjevu 1, naznačen time, da je to (2R)-2-{(S)-6,7-dimetoksi-1-[2-(4- trifluorometil-fenil)-etil]-3,4-dihidro-1H-izokinolin-2-il}-N-metil-2-fenil-acetamid-sol klorovodične kiseline.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da se upotrebljava kao lijek.
6. Farmaceutski sastav, naznačen time, da obuhvaća najmanje jedan spoj prema bilo kojem od zahtjeva 1 do 4 i farmaceutski prihvatljiv prijenosni materijal.
7. Uporaba spoja prema bilo kojem od zahtjeva 1 do 4, naznačen time, da je za proizvodnju lijeka za prevenciju ili liječenje poremećaja ili bolesti odabrane iz skupine koju čine poremećaji hranjenja i poremećaji spavanja.
8. Uporaba prema zahtjevu 7, naznačen time, da poremećaji hranjenja obuhvaćaju metaboličku disfunkciju, kompulzivne pretilosti, emeto-bulimiju ili anoreksiju zbog nervnog poremećaja.
9. Uporaba prema zahtjevu 7, naznačen time, da poremećaj ili bolest je poremećaj spavanja.
10. Uporaba prema zahtjevu 9, naznačen time, da navedeni poremećaj spavanja obuhvaća nesanice, narkolepsiju i ostale poremećaje pretjerane pospanosti, distonije povezane sa spavanjem, sindrom nemirnih nogu, apneje u spavanju, sindrom "jet-lag" (kliničko stanje poremećaja dnevnog ritma spavanja zbog putovanja kroz vremenske zone), sindrom "shift- work" (kliničko stanje poremećaja dnevnog ritma spavanja zbog rada u smjenama), sindrom zakašnjelog ili preuranjenog vremena spavanja.
11. Uporaba prema zahtjevu 9, naznačen time, da navedeni poremećaj spavanja je nesanica.
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EP2004002020 | 2004-03-01 | ||
PCT/EP2005/001879 WO2005118548A1 (en) | 2004-03-01 | 2005-02-23 | Substituted 1,2,3,4-tetrahydroisoquinoline derivatives |
EP05804734.1A EP1751111B1 (en) | 2004-03-01 | 2005-02-23 | Substituted 1,2,3,4-tetrahydroisoquinoline derivatives |
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HRP20150371T1 true HRP20150371T1 (hr) | 2015-05-08 |
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HRP20150371TT HRP20150371T1 (hr) | 2004-03-01 | 2015-03-30 | Supstituirani derivati 1,2,3,4-tetrahidroizokinolina |
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US (2) | US7763638B2 (hr) |
EP (1) | EP1751111B1 (hr) |
JP (1) | JP4094050B2 (hr) |
KR (1) | KR100848747B1 (hr) |
CN (1) | CN1926109B (hr) |
AR (1) | AR047823A1 (hr) |
AU (1) | AU2005250077B2 (hr) |
BR (1) | BRPI0508263B8 (hr) |
CA (1) | CA2557163C (hr) |
CY (1) | CY1116103T1 (hr) |
DK (1) | DK1751111T3 (hr) |
ES (1) | ES2533389T3 (hr) |
HR (1) | HRP20150371T1 (hr) |
IL (1) | IL177798A (hr) |
MY (1) | MY144992A (hr) |
NO (1) | NO337299B1 (hr) |
NZ (1) | NZ550216A (hr) |
PL (1) | PL1751111T3 (hr) |
PT (1) | PT1751111E (hr) |
RU (1) | RU2378257C2 (hr) |
SI (1) | SI1751111T1 (hr) |
TW (1) | TWI301129B (hr) |
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-
2005
- 2005-02-23 WO PCT/EP2005/001879 patent/WO2005118548A1/en active Application Filing
- 2005-02-23 RU RU2006134624/04A patent/RU2378257C2/ru active
- 2005-02-23 SI SI200531944T patent/SI1751111T1/sl unknown
- 2005-02-23 EP EP05804734.1A patent/EP1751111B1/en active Active
- 2005-02-23 US US10/598,449 patent/US7763638B2/en active Active
- 2005-02-23 JP JP2007501172A patent/JP4094050B2/ja active Active
- 2005-02-23 AU AU2005250077A patent/AU2005250077B2/en active Active
- 2005-02-23 KR KR1020067020299A patent/KR100848747B1/ko active IP Right Grant
- 2005-02-23 PT PT58047341T patent/PT1751111E/pt unknown
- 2005-02-23 DK DK05804734.1T patent/DK1751111T3/en active
- 2005-02-23 PL PL05804734T patent/PL1751111T3/pl unknown
- 2005-02-23 ES ES05804734.1T patent/ES2533389T3/es active Active
- 2005-02-23 BR BRPI0508263-3 patent/BRPI0508263B8/pt active IP Right Grant
- 2005-02-23 CN CN200580006491XA patent/CN1926109B/zh active Active
- 2005-02-23 CA CA2557163A patent/CA2557163C/en active Active
- 2005-02-23 NZ NZ550216A patent/NZ550216A/en unknown
- 2005-02-28 MY MYPI20050816A patent/MY144992A/en unknown
- 2005-02-28 AR ARP050100745A patent/AR047823A1/es unknown
- 2005-03-01 TW TW094106070A patent/TWI301129B/zh active
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2006
- 2006-08-21 ZA ZA200606974A patent/ZA200606974B/xx unknown
- 2006-08-31 IL IL177798A patent/IL177798A/en active IP Right Grant
- 2006-09-26 NO NO20064347A patent/NO337299B1/no unknown
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2010
- 2010-06-15 US US12/815,605 patent/US20100256182A1/en not_active Abandoned
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2015
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- 2015-03-30 HR HRP20150371TT patent/HRP20150371T1/hr unknown
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