JP2018522032A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018522032A5 JP2018522032A5 JP2018504985A JP2018504985A JP2018522032A5 JP 2018522032 A5 JP2018522032 A5 JP 2018522032A5 JP 2018504985 A JP2018504985 A JP 2018504985A JP 2018504985 A JP2018504985 A JP 2018504985A JP 2018522032 A5 JP2018522032 A5 JP 2018522032A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- azaspiro
- octane
- piperidin
- ethyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 25
- 125000005842 heteroatom Chemical group 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 22
- 229910052717 sulfur Inorganic materials 0.000 claims 22
- 229910052760 oxygen Inorganic materials 0.000 claims 21
- 125000001153 fluoro group Chemical group F* 0.000 claims 16
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 15
- 150000002430 hydrocarbons Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- -1 cyano, hydroxy, amino Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 208000002193 Pain Diseases 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 208000000094 Chronic Pain Diseases 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 206010065390 Inflammatory pain Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 208000005298 acute pain Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 230000002981 neuropathic effect Effects 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000006001 difluoroethyl group Chemical group 0.000 claims 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000005976 1-phenylethyloxy group Chemical group 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- AJIPGNUNWQKPLB-UHFFFAOYSA-N ethyl 2-[4-[acetyl(1,3-oxazol-2-ylmethyl)amino]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CC=1OC=CN=1 AJIPGNUNWQKPLB-UHFFFAOYSA-N 0.000 claims 1
- IIKLTKOTICGSHO-UHFFFAOYSA-N ethyl 2-[4-[acetyl(2-methylpropyl)amino]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CC(C)C IIKLTKOTICGSHO-UHFFFAOYSA-N 0.000 claims 1
- SVLHLBHIUNWCMN-UHFFFAOYSA-N ethyl 2-[4-[acetyl(cyclopropylmethyl)amino]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CC1CC1 SVLHLBHIUNWCMN-UHFFFAOYSA-N 0.000 claims 1
- GWYMXLWBAKWFDE-UHFFFAOYSA-N ethyl 6-[4-[acetyl(cyclopropyl)amino]piperidin-1-yl]-2-azaspiro[3.4]octane-2-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(CN(C2)C(=O)OCC)CC1)C1CC1 GWYMXLWBAKWFDE-UHFFFAOYSA-N 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 230000003551 muscarinic effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CCC1C(C)(*)C[C@@]1CN(C)C1*(C)CC(*)C(CC2)(CN2C(O)OC*)C1 Chemical compound CCC1C(C)(*)C[C@@]1CN(C)C1*(C)CC(*)C(CC2)(CN2C(O)OC*)C1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1513742.5A GB201513742D0 (en) | 2015-08-03 | 2015-08-03 | Muscarinic agonists |
| GB1513742.5 | 2015-08-03 | ||
| PCT/GB2016/052386 WO2017021730A1 (en) | 2015-08-03 | 2016-08-03 | Muscarinic agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018522032A JP2018522032A (ja) | 2018-08-09 |
| JP2018522032A5 true JP2018522032A5 (enExample) | 2019-08-29 |
| JP6876675B2 JP6876675B2 (ja) | 2021-05-26 |
Family
ID=54063148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018504985A Active JP6876675B2 (ja) | 2015-08-03 | 2016-08-03 | ムスカリンアゴニスト |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US9758506B2 (enExample) |
| EP (2) | EP3822262B1 (enExample) |
| JP (1) | JP6876675B2 (enExample) |
| KR (1) | KR102664558B1 (enExample) |
| CN (1) | CN107949558B (enExample) |
| AR (1) | AR105593A1 (enExample) |
| AU (1) | AU2016302048B2 (enExample) |
| BR (1) | BR112018002279B1 (enExample) |
| CA (1) | CA2993484C (enExample) |
| CL (1) | CL2018000292A1 (enExample) |
| CO (1) | CO2018002060A2 (enExample) |
| DK (1) | DK3331869T3 (enExample) |
| ES (2) | ES2850298T3 (enExample) |
| GB (1) | GB201513742D0 (enExample) |
| IL (1) | IL257064A (enExample) |
| MX (1) | MX379530B (enExample) |
| MY (1) | MY195244A (enExample) |
| PH (1) | PH12018500259A1 (enExample) |
| RU (1) | RU2737158C2 (enExample) |
| TW (1) | TWI723037B (enExample) |
| UA (1) | UA123315C2 (enExample) |
| WO (1) | WO2017021730A1 (enExample) |
| ZA (1) | ZA201800715B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2619829T3 (es) | 2011-11-18 | 2017-06-27 | Heptares Therapeutics Limited | Agonistas del receptor muscarínico M1 |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513742D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| CN108137547B (zh) | 2015-08-03 | 2021-11-12 | 百时美施贵宝公司 | 可用作TNFα调节剂的杂环化合物 |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| HUE048902T2 (hu) | 2015-08-03 | 2020-08-28 | Glenmark Pharmaceuticals Sa | Új ROR gamma modulátor vegyületek |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| EP3394061B1 (en) | 2015-12-23 | 2020-03-11 | Merck Sharp & Dohme Corp. | 6,7-dihydro-5h-pyrrolo[3,4-b]pyridin-5-one allosteric modulators of the m4 muscarinic acetylcholine receptor |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| WO2019000237A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000238A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | 5- (PYRIDIN-3-YL) OXAZOLE ALLOSTERIC MODULATORS OF M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000236A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| EP3651762B1 (en) | 2017-07-12 | 2024-07-03 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| CN110944999A (zh) * | 2017-08-01 | 2020-03-31 | 勃林格殷格翰国际有限公司 | 中间体化合物和方法 |
| WO2019079410A1 (en) | 2017-10-17 | 2019-04-25 | Vanderbilt University | ANTAGONISTS OF THE MUSCARINIC RECEPTOR OF ACETYLCHOLINE M4 |
| JP7270989B2 (ja) | 2017-10-20 | 2023-05-11 | ヴァンダービルト ユニバーシティー | ムスカリン性アセチルコリン受容体ｍ４のアンタゴニスト |
| EP3732163A4 (en) * | 2017-12-20 | 2021-07-14 | Vanderbilt University | MUSCARIN M4 ACETYLCHOLIN RECEPTOR ANTAGONISTS |
| EP3768669B1 (en) * | 2018-03-23 | 2023-01-25 | Pfizer Inc. | Piperazine azaspiro derivaves |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201810245D0 (en) * | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| PH12022550860A1 (en) | 2019-10-09 | 2023-06-14 | Novartis Ag | 5-oxa-2-azaspiro[3.4]octane derivatives as m4 agonists |
| UY38906A (es) * | 2019-10-09 | 2021-05-31 | Novartis Ag | Compuestos 2- derivados de azaspiro[3,4]octano como agonistas de m4 y composiciones de los mismos |
| US20250064833A1 (en) | 2021-12-13 | 2025-02-27 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2008137583A (ru) * | 2006-02-22 | 2010-03-27 | Вертекс Фармасьютикалз Инкорпорейшн (Us) | Спиропиперидины в качестве модуляторов мускариновых рецепторов |
| US20090221567A1 (en) * | 2008-02-28 | 2009-09-03 | Astrazeneca Ab | Muscarinic receptor agonists, compositions, methods of treatment thereof, and processes for preparation thereof 177 |
| US20130197027A1 (en) * | 2010-03-10 | 2013-08-01 | Craig Lindsley | Heterocyclyl-azabicyclo[3.2.1]octane analogs as selective m1 agonists and methods of making and using same |
| ES2619829T3 (es) * | 2011-11-18 | 2017-06-27 | Heptares Therapeutics Limited | Agonistas del receptor muscarínico M1 |
| EP2897948B1 (en) * | 2012-09-18 | 2016-08-31 | Heptares Therapeutics Limited | Bicyclic aza compounds as muscarinic m1 receptor agonists |
| RU2685230C2 (ru) | 2014-02-06 | 2019-04-17 | Хептарес Терапьютикс Лимитед | Бициклические азотсодержащие соединения как агонисты М1 мускариновых рецепторов |
| CN108137547B (zh) | 2015-08-03 | 2021-11-12 | 百时美施贵宝公司 | 可用作TNFα调节剂的杂环化合物 |
| GB201513742D0 (en) * | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| AR105556A1 (es) | 2015-08-03 | 2017-10-18 | Hoffmann La Roche | Derivados de etinilo |
| HUE048902T2 (hu) | 2015-08-03 | 2020-08-28 | Glenmark Pharmaceuticals Sa | Új ROR gamma modulátor vegyületek |
-
2015
- 2015-08-03 GB GBGB1513742.5A patent/GB201513742D0/en not_active Ceased
-
2016
- 2016-08-03 AU AU2016302048A patent/AU2016302048B2/en active Active
- 2016-08-03 KR KR1020187006156A patent/KR102664558B1/ko active Active
- 2016-08-03 BR BR112018002279-9A patent/BR112018002279B1/pt active IP Right Grant
- 2016-08-03 EP EP20213929.1A patent/EP3822262B1/en active Active
- 2016-08-03 AR ARP160102378A patent/AR105593A1/es unknown
- 2016-08-03 JP JP2018504985A patent/JP6876675B2/ja active Active
- 2016-08-03 MX MX2018001564A patent/MX379530B/es unknown
- 2016-08-03 WO PCT/GB2016/052386 patent/WO2017021730A1/en not_active Ceased
- 2016-08-03 RU RU2018105020A patent/RU2737158C2/ru active
- 2016-08-03 MY MYPI2018000148A patent/MY195244A/en unknown
- 2016-08-03 ES ES16750223T patent/ES2850298T3/es active Active
- 2016-08-03 US US15/227,325 patent/US9758506B2/en active Active
- 2016-08-03 DK DK16750223.6T patent/DK3331869T3/da active
- 2016-08-03 TW TW105124670A patent/TWI723037B/zh active
- 2016-08-03 EP EP16750223.6A patent/EP3331869B1/en active Active
- 2016-08-03 UA UAA201801267A patent/UA123315C2/uk unknown
- 2016-08-03 CA CA2993484A patent/CA2993484C/en active Active
- 2016-08-03 ES ES20213929T patent/ES2980578T3/es active Active
- 2016-08-03 CN CN201680043661.XA patent/CN107949558B/zh active Active
-
2017
- 2017-09-08 US US15/699,674 patent/US10351545B2/en active Active
-
2018
- 2018-01-21 IL IL257064A patent/IL257064A/en unknown
- 2018-02-01 CL CL2018000292A patent/CL2018000292A1/es unknown
- 2018-02-01 US US15/886,057 patent/US10167272B2/en active Active
- 2018-02-02 ZA ZA2018/00715A patent/ZA201800715B/en unknown
- 2018-02-02 PH PH12018500259A patent/PH12018500259A1/en unknown
- 2018-02-26 CO CONC2018/0002060A patent/CO2018002060A2/es unknown
-
2019
- 2019-05-21 US US16/418,354 patent/US11091456B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2018105020A (ru) | Агонисты мускариновых рецепторов | |
| JP2018536653A5 (enExample) | ||
| JP2008513499A5 (enExample) | ||
| TWI387592B (zh) | 經取代之苯并咪唑及其作為與腫瘤形成相關激酶之抑制劑之方法 | |
| JP2015501799A5 (enExample) | ||
| JP2018522034A5 (enExample) | ||
| RU2424240C2 (ru) | Антибактериальные производные пиперидина | |
| JP2018511587A5 (enExample) | ||
| JP2008513516A5 (enExample) | ||
| HRP20201171T1 (hr) | Derivati izoindolin-1-ona kao modulatori aktivnosti pozitivnog alosternog modulatora kolinergijskog muskarinskog m1 receptora za liječenje alzheimerove bolesti | |
| JP2018519323A5 (enExample) | ||
| JP2006206609A5 (enExample) | ||
| JP2016014037A (ja) | 縮合複素環式化合物およびそれらの使用 | |
| JP2008513515A5 (enExample) | ||
| JP2016169231A (ja) | Ｍｇｌｕｒ５の負のアロステリック調節剤としての６−アルキル−ｎ−（ピリジン−２−イル）−４−アリールオキシピコリンアミド類似体ならびにそれを作製および使用する方法 | |
| HRP20100522T1 (hr) | Piridin karboksamidi kao inhibitori 11-beta-hsd1 | |
| JP2018515489A5 (enExample) | ||
| JP2009524670A5 (enExample) | ||
| JP2018524338A5 (enExample) | ||
| RU2011134868A (ru) | N-замещенные насыщенные гетероциклические сульфоновые соединения с активностью агонистов рецептора св2 | |
| CA2657106A1 (en) | Aminoindane derivative or salt thereof | |
| JPWO2015182723A1 (ja) | 新規ピロリジン化合物およびメラノコルチン受容体作動薬としての用途 | |
| HRP20161797T1 (hr) | Spojevi 1,3-oksazolidina ili 1,3-oksazinana kao antagonisti receptora oreksina | |
| KR20150120516A (ko) | 2-아실아미노티아졸 유도체 또는 그의 염 | |
| HRP20140588T1 (hr) | Spojevi kondenziranog prstena i njihova uporaba |