HRP20120920T1 - Spojevi 4-[2-(2 fluorofenoksimetil)fenil]piperidina - Google Patents
Spojevi 4-[2-(2 fluorofenoksimetil)fenil]piperidina Download PDFInfo
- Publication number
- HRP20120920T1 HRP20120920T1 HRP20120920AT HRP20120920T HRP20120920T1 HR P20120920 T1 HRP20120920 T1 HR P20120920T1 HR P20120920A T HRP20120920A T HR P20120920AT HR P20120920 T HRP20120920 T HR P20120920T HR P20120920 T1 HRP20120920 T1 HR P20120920T1
- Authority
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- Croatia
- Prior art keywords
- fluoro
- hydrogen
- chloro
- compound according
- difluoro
- Prior art date
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- KXUVOOVIGIJFNL-UHFFFAOYSA-N 4-[2-[(2-fluorophenoxy)methyl]phenyl]piperidine Chemical class FC1=CC=CC=C1OCC1=CC=CC=C1C1CCNCC1 KXUVOOVIGIJFNL-UHFFFAOYSA-N 0.000 title 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- 125000001309 chloro group Chemical group Cl* 0.000 claims 24
- 150000002431 hydrogen Chemical class 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000001246 bromo group Chemical group Br* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 208000027520 Somatoform disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000027753 pain disease Diseases 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- -1 t-butoxycarbonyl Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 208000008930 Low Back Pain Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 229940127450 Opioid Agonists Drugs 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 claims 1
- 239000000219 Sympatholytic Substances 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 229940125681 anticonvulsant agent Drugs 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 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
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000009977 dual effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000009245 menopause Effects 0.000 claims 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 1
- 239000003887 narcotic antagonist Substances 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 1
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 claims 1
- 239000003195 sodium channel blocking agent Substances 0.000 claims 1
- 230000000948 sympatholitic effect Effects 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000001457 vasomotor Effects 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
-
- A—HUMAN NECESSITIES
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4465—Non condensed piperidines, e.g. piperocaine only substituted in position 4
-
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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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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Claims (30)
1. Spoj formule I:
[image]
naznačen time, da: a je 0, 1, 2, 3, ili 4; svaki R1 je neovisno halo ili trifluorometil; R3
je vodik, halo, ili –C1-6alkil; R4,, R5, i R6, su neovisno vodik ili halo; ili njihova
farmaceutski prihvatljiva sol.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da je R3 vodik, fluoro, kloro ili metil.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da je R4 vodik, fluoro, kloro ili bromo.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da je R5 vodik ili fluoro.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da je R6 vodik, fluoro, kloro ili bromo.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da a jeste 0.
7. Spoj u skladu s patentnim zahtjevom 6, naznačen time, da je R3 vodik, fluoro, kloro ili metil; R4 je vodik, fluoro, kloro ili bromo; R5 je vodik ili fluoro; a R6 je vodik, fluoro, kloro ili bromo.
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da a je 0, R3 i R5 su vodik a R4 i R6 su fluoro.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da a jeste 1.
10. Spoj u skladu s patentnim zahtjevom 9, naznačen time, da R1 je 3-fluoro, 4- fluoroo, 5-fluoro, 5-trifluorometil ili6-fluoro.
11. Spoj u skladu s patentnim zahtjevom 9, naznačen time, da R3 je vodik ili fluoro; R4 je vodik ili fluoro; R5 je vodik ili fluoro; i R6 je vodik, fluoro ili kloro.
12. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da a jeste 2.
13. Spoj u skladu s patentnim zahtjevom 12, naznačen time, da R1 je 4,5-difluoro, 4,6-difluoro ili 5,6-difluoro.
14. Spoj u skladu s patentnim zahtjevom 12, naznačen time, da R3 je vodik ili fluoro; R4 je vodik ili fluoro; R5 je vodik ili fluoroo; i R6 je vodik, fluoro ili kloro.
15. Spoj formule II u skladu s patentnim zahtjevom 1:
[image]
naznačen time, da:
(a) R3 i R5 su vodik a:
(i) R4 je fluoro, R6 je fluoro i a jeste 0;
(ii) R4 je fluoro, R5 je fluoro, a jeste 1, a R1 je 4-fluoro, 5-fluoro, 5-trifluorometil ili 6- fluoro;
(iii) R4 je fluoro, R6 je fluoro, a jeste 2 a R1 je 4,5-difluoro, 4,6-difluoro ili 5,6-difluoro;
(iv) R4 je fluoro, R6 je kloro, i a jeste 0;
(v) R4 je kloro, R6 je fluoro i a jeste 0; ili
(vi) R4 je bromo, R6 je kloro i a jeste 0; ili
(b) R3 i R4 su vodik, R5 je fluoro, R6 je kloro, a:
(i) a je 0;
(ii) a je 1 i R1 je 5-fluoro ili 6-fluoro; ili
(iii) a je 2 i R1 je 4,6-difluoro; ili
(c) R4 i R5 su vodik, R6 je fluoro i;
(i) R3 je fluoro i a jeste 0;
(ii) R3 je fluoro, a jeste 1 i R1 je 3-fluoro, 5-fluoro, 5- trifluorometil ili 6-fluoro;
(iii) R3 je fluoro, a jeste 2 i R1 je 4,6-difluoro; ili
(iv) R3 je kloro ili metil i a jeste 0; ili
(d) R3, R4 i R5 su vodik a:
(i) R6 je H i a jeste 0;
(ii) R6 je H, a jeste 1 a R1 je 5-fluoro ili 6-fluoro;
(iii) R6 je fluoro i a jeste 0;
(iv) R6 je fluoro, a jeste 1 i R1 je 4-fluoro, 5-fluoro ili 6-fluoro;
(v) R6 je fluoro, a jeste 2 i R1 je 4,5-difluoro ili 4,6-difluoro;
(vi) R6 je kloro i a jeste 0;
(vii) R6 je kloro, a jeste 1 i R1 je 4-fluoro, 6-fluoro ili 5-trifluorometil;
(viii) R6 je kloro, a jeste 2 i R1 je 4,5-difluoro; ili
(ix) R6 je bromo i a jeste 0;
ili njihova farmaceutski prihvatljiva sol.
16. Spoj u skladu s patentnim zahtjevom 15, naznačen time, da su R3 i R5 vodik, i:
(i) R4 je fluoro, R6 je fluoro, i a je 0;
(ii) R4 je fluoro, R6 je fluoro, a je 1, a R1 je 4-tluoro, 5-fluoro, 5-trifluorometil ili 6-fluoro;
(iii) R4 je fluoro, R6 je fluoro, a je 2 i R1 je 4,5-difluoro, 4.6-difluoro ili 5,6-difluoro;
(iv) R4 je fluoro, R6 je kloro i a je 0;
(v) R4 je kloro, R6 je fluoro i a je 0; ili
(vi) R4 je bromo, R5 je kloro, i a je 0.
17. Spoj u skladu s patentnim zahtjevom 16, naznačene time, da je R4 fluoro, R6 je fluoro i a je 0.
18. Spoj u skladu s patentnim zahtjevom 15, naznačen time, da su R3 i R4 vodik, R5 je fluoro, R6 je kloro, i:
(i) a je 0;
(ii) a je 1 i R1 je 5-fluoro ili 6-fluoro; ili
(iii) a je 2 i R1 je 4,6-difluoro.
19. Spoj u skladu s patentnim zahtjevom 15, naznačen time, da su R4 i R5 vodik, R6 je fluoro, i;
(i) R3 je fluoro i a je 0;
(ii) R3 je fluoro, a je 1 i R1 je 3-fluoro, 5-fluoro, 5- trifluorometil ili 6-fluoro;
(iii) R3 je fluoro, a je 2 i R1 je 4,6-diftuoro; ili
(iv) R3 je kloro ili metil i a je 0.
20. Spoj u skladu s patentnim zahtjevom 15, naznačen time, da su R3, R4, i R5 vodik, a:
(i) R6 je H i a je 0;
(ii) R6 je H, a je 1 i R1 je 5-fluoro ili 6-fluoro;
(iii) R6 je fluoro i a je 0;
(iv) R6 je fluoro, a je 1 i R1 je 4-fluoro, 5-fluoro ili 6-fluoro;
(v) R6 je fluoro, a je 2 i R1 je 4,5-difluoro ili 4,6-difluoro;
(vi) R6 je kloro i a je 0;
(vii) R6 je kloro, a je 1 i R1 je 4-fluoro, 6-fluoro ili 5-trifluorometil;
(viii) R6 je kloro, a je 2 i R1 je 4,5-difluoro; ili
(ix) R6 je bromo i a je 0.
21. Spoj formule III, koristan u sintezi spoja iz bilo kojeg od patentnih zahtjeva 1 do 20:
[image]
naznačen time, da P predstavlja amino-zaštitnu skupinu odabranu od t-butoksickrbonila, tritila, benziloksikarbonila, 9-fluoroenilmetoksikarbonila, formila i benzila; ili njihove soli.
22. Spoj u skladu s patentnim zahtjevom 21, naznačen time, da a je 0, R3 i R5 su vodik a R4 i R6 su fluoro.
23. Postupak priprave spoje prema bilo kojem od patentnih zahtjeva 1 do 20, gdje se postupak sastoji od deprotekcije spoja formule III:
[image]
ili njegove soli, naznačen time, da P predstavlja amino-zaštitnu skupinu, kako bi se dobio spoj formule II ili I.
24. Postupak prema patentnom zahtjevu 23, naznačen time, da a jeste 0, R3 i R5 su vodik a R4 i R6 su fluoro.
25. Farmaceutski pripravak, naznačen time, da sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 20 i farmaceutski prihvatljiv nosač, koji po izboru dalje može sadržavati drugo terapijsko sredstvo.
26. Farmaceutski pripravak u skladu s patentnim zahtjevom 25, naznačen time, da je nazočno drugo terapijsko sredstvo i da je odabrano od sredstava protiv Alzheimerove bolesti, antikonvulzanata, antidepresiva, sredstava protiv Parkinsonove bolesti, dvojnih serotonin-norepinefrinskih povratnih inhibitora, nesteroidnih protu-upalnih sredstava, norepinefrinskih povratnih inhibitora, opioidnih agonista, opioidnih antagonista, selektivnih serotonininskih povratnih inhibitora, blokatora natrijevih kanala, simpatolitika i njihovih kombinacija.
27. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 20, naznačen time, da je za uporabu u liječenju.
28. Spoj u skladu s patentnim zahtjevom 27, naznačen time, da se koristi za liječenje poremećaja boli, poremećaja depresije, afektivnog poremećaja, poremećaja pažnje uslijed hiperaktivnosti, kognitivnog poremećaja, urinarne inkontinencije uzrokovane stresom, sindroma kroničnog umora, pretilosti i vazomotornih simptoma povezanih s menopauzom.
29. Spoj u skladu s patentnim zahtjevom 28, naznačen time, da je poremećaj boli neuropatska bol ili fibromijalgija.
30. Spoj u skladu s patentnim zahtjevom 27, naznačen time, da se koristi za liječenje kronične križobolje ili osteoartritisa.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11454108P | 2008-11-14 | 2008-11-14 | |
| PCT/US2009/064308 WO2010056941A1 (en) | 2008-11-14 | 2009-11-13 | 4-[2-(2-fluorophenoxymethyl)phenyl]piperidine compounds |
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| Publication Number | Publication Date |
|---|---|
| HRP20120920T1 true HRP20120920T1 (hr) | 2013-01-31 |
Family
ID=41666409
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| Application Number | Title | Priority Date | Filing Date |
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| HRP20120897AT HRP20120897T1 (hr) | 2008-11-14 | 2012-11-07 | Kristalni oblik spoja 4-[2-(2-fluorofenoksimetil)fenil]piperidina |
| HRP20120920AT HRP20120920T1 (hr) | 2008-11-14 | 2012-11-13 | Spojevi 4-[2-(2 fluorofenoksimetil)fenil]piperidina |
| HRP20130300AT HRP20130300T1 (hr) | 2008-11-14 | 2013-04-02 | Postupak za pripravu 4-[2-(2-fluorofenoksimetil)fenil]piperidin spojeva |
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| HRP20130300AT HRP20130300T1 (hr) | 2008-11-14 | 2013-04-02 | Postupak za pripravu 4-[2-(2-fluorofenoksimetil)fenil]piperidin spojeva |
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| BR (3) | BRPI0921593B8 (hr) |
| CA (3) | CA2739992C (hr) |
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| HR (3) | HRP20120897T1 (hr) |
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| PL (3) | PL2358674T3 (hr) |
| PT (3) | PT2358674E (hr) |
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| SI (3) | SI2358675T1 (hr) |
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| TW (3) | TWI441810B (hr) |
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| US8778949B2 (en) | 2010-01-11 | 2014-07-15 | Theravance Biopharma R&D Ip, Llc | 1-(2-phenoxymethylphenyl)piperazine compounds |
| ES2543064T3 (es) * | 2010-03-22 | 2015-08-14 | Theravance Biopharma R&D Ip, Llc | Compuestos de 1-(2-fenoximetilheteroaril)piperidina y piperazina |
| RU2012149695A (ru) * | 2010-04-22 | 2014-05-27 | Тереванс, Инк. | Комбинация ингибитора обратного захвата серотонина и норэпинефрина и опиодного агониста для лечения боли |
| JP6277121B2 (ja) | 2011-03-22 | 2018-02-07 | アドヴィナス・セラピューティックス・リミテッド | 置換された縮合三環式化合物、その組成物および医学的応用 |
| US9544692B2 (en) * | 2012-11-19 | 2017-01-10 | Bitwave Pte Ltd. | System and apparatus for boomless-microphone construction for wireless helmet communicator with siren signal detection and classification capability |
| AU2017321016B2 (en) * | 2016-08-30 | 2020-04-23 | Theravance Biopharma R&D Ip, Llc | Compound for use in the treatment of neurogenic orthostatic hypotension |
| WO2019232010A1 (en) | 2018-06-01 | 2019-12-05 | Theravance Biopharma R&D Ip, Llc | PROCESS FOR PREPARING 2-(1-(tert-BUTOXYCARBONYL)PIPERIDINE-4-YL)BENZOIC ACID |
| AU2023241617A1 (en) | 2022-03-28 | 2024-09-05 | Theravance Biopharma R&D Ip, Llc | Ampreloxetine for use for treating multiple system atrophy |
| CN114957098B (zh) * | 2022-06-02 | 2024-03-29 | 和鼎（南京）医药技术有限公司 | 一种制备喷他佐辛中间体的方法 |
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- 2012-01-26 HK HK12100743.6A patent/HK1160449A1/xx not_active IP Right Cessation
- 2012-01-27 HK HK12100779.3A patent/HK1160452A1/xx unknown
- 2012-07-10 US US13/545,513 patent/US8802857B2/en active Active
- 2012-09-28 US US13/631,192 patent/US8604058B2/en active Active
- 2012-10-01 US US13/632,588 patent/US8592596B2/en active Active
- 2012-11-07 HR HRP20120897AT patent/HRP20120897T1/hr unknown
- 2012-11-13 HR HRP20120920AT patent/HRP20120920T1/hr unknown
- 2012-11-29 CY CY20121101168T patent/CY1113622T1/el unknown
- 2012-12-07 CY CY20121101189T patent/CY1113623T1/el unknown
- 2012-12-27 SM SM201200063T patent/SMT201200063B/it unknown
- 2012-12-28 SM SM201200065T patent/SMT201200065B/xx unknown
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2013
- 2013-03-26 SM SM201300033T patent/SMT201300033B/xx unknown
- 2013-03-26 CY CY20131100256T patent/CY1113855T1/el unknown
- 2013-04-02 HR HRP20130300AT patent/HRP20130300T1/hr unknown
- 2013-10-23 US US14/060,846 patent/US9073859B2/en active Active
- 2013-11-04 US US14/070,887 patent/US9162982B2/en active Active
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2014
- 2014-02-25 JP JP2014033727A patent/JP2014098033A/ja not_active Withdrawn
- 2014-03-07 JP JP2014044653A patent/JP2014101384A/ja not_active Withdrawn
- 2014-03-12 JP JP2014048387A patent/JP2014139209A/ja not_active Withdrawn
- 2014-07-08 US US14/325,863 patent/US9187423B2/en active Active
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2015
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2017
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2018
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2019
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2020
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2021
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2023
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2024
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