JP2004506611A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004506611A5 JP2004506611A5 JP2002501887A JP2002501887A JP2004506611A5 JP 2004506611 A5 JP2004506611 A5 JP 2004506611A5 JP 2002501887 A JP2002501887 A JP 2002501887A JP 2002501887 A JP2002501887 A JP 2002501887A JP 2004506611 A5 JP2004506611 A5 JP 2004506611A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- optionally
- unsubstituted
- tricyclo
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 239000012453 solvate Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 0 CNc1c(*)cnc(**)c1* Chemical compound CNc1c(*)cnc(**)c1* 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- -1 cyano, nitro, amino, hydroxyl Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- ZZCFIJUBAKINHP-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-(piperidin-4-ylmethylamino)pyridine-4-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=CN=C1NCC1CCNCC1 ZZCFIJUBAKINHP-UHFFFAOYSA-N 0.000 description 2
- SRZWNZWESNFUCG-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-piperazin-2-ylpyridine-4-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=CN=C1C1CNCCN1 SRZWNZWESNFUCG-UHFFFAOYSA-N 0.000 description 2
- 230000000414 obstructive effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 1
- GFOVTTQVBDEYPP-UHFFFAOYSA-N 2,5-dichloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=NC=C1Cl GFOVTTQVBDEYPP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DLHGEIMBTIHQGR-UHFFFAOYSA-N CC1(CC2)CCN2CC1 Chemical compound CC1(CC2)CCN2CC1 DLHGEIMBTIHQGR-UHFFFAOYSA-N 0.000 description 1
- MWBULQNPGVGHKO-UHFFFAOYSA-N CC1C(CC2)CCN2C1 Chemical compound CC1C(CC2)CCN2C1 MWBULQNPGVGHKO-UHFFFAOYSA-N 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N CC1CCC(C)CC1 Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N CC1CCNCC1 Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- KYINPWAJIVTFBW-UHFFFAOYSA-N CC1CNCC1 Chemical compound CC1CNCC1 KYINPWAJIVTFBW-UHFFFAOYSA-N 0.000 description 1
- JEGMWWXJUXDNJN-UHFFFAOYSA-N CC1CNCCC1 Chemical compound CC1CNCCC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 1
- VMJOIXFVKVPLRQ-UHFFFAOYSA-N CC1CNCCNC1 Chemical compound CC1CNCCNC1 VMJOIXFVKVPLRQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- QAJXMZULCNFSHV-UHFFFAOYSA-N ClC=1C(=CC(=NC1)OCCC1CCNCC1)C(=O)NCC12CC3CC(CC(C1)C3)C2 Chemical compound ClC=1C(=CC(=NC1)OCCC1CCNCC1)C(=O)NCC12CC3CC(CC(C1)C3)C2 QAJXMZULCNFSHV-UHFFFAOYSA-N 0.000 description 1
- JYNKPVLADAJCFW-UHFFFAOYSA-N ClC=1C(=CC(=NC1)OCCC1CNCCC1)C(=O)NCC12CC3CC(CC(C1)C3)C2 Chemical compound ClC=1C(=CC(=NC1)OCCC1CNCCC1)C(=O)NCC12CC3CC(CC(C1)C3)C2 JYNKPVLADAJCFW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 208000006673 asthma Diseases 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SMGASZAURPOVAV-UHFFFAOYSA-N n-(1-adamantylmethyl)-2,5-dichloropyridine-4-carboxamide Chemical compound C1=NC(Cl)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl SMGASZAURPOVAV-UHFFFAOYSA-N 0.000 description 1
- NKGZBWBOASPWEV-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-(3-aminopyrrolidin-1-yl)-5-chloropyridine-4-carboxamide Chemical compound C1C(N)CCN1C1=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C(Cl)C=N1 NKGZBWBOASPWEV-UHFFFAOYSA-N 0.000 description 1
- DCWLWVQKMUBEHU-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-(4-aminopiperidin-1-yl)-3-chloropyridine-4-carboxamide Chemical compound C1CC(N)CCN1C1=NC=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl DCWLWVQKMUBEHU-UHFFFAOYSA-N 0.000 description 1
- GUCPGAHGJHRKBV-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-(4-aminopiperidin-1-yl)-5-chloropyridine-4-carboxamide Chemical compound C1CC(N)CCN1C1=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C(Cl)C=N1 GUCPGAHGJHRKBV-UHFFFAOYSA-N 0.000 description 1
- ULQNKQVYRQIHGV-UHFFFAOYSA-N n-(1-adamantylmethyl)-3-chloro-2-(piperidin-4-ylmethylamino)pyridine-4-carboxamide Chemical compound N1=CC=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=C1NCC1CCNCC1 ULQNKQVYRQIHGV-UHFFFAOYSA-N 0.000 description 1
- IUNICHLZTMQOGZ-UHFFFAOYSA-N n-(1-adamantylmethyl)-3-chloro-2-piperazin-2-ylpyridine-4-carboxamide Chemical compound N1=CC=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=C1C1CNCCN1 IUNICHLZTMQOGZ-UHFFFAOYSA-N 0.000 description 1
- LHDSEYVQXPLPAK-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-(1,4-diazepan-1-yl)pyridine-4-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=CN=C1N1CCCNCC1 LHDSEYVQXPLPAK-UHFFFAOYSA-N 0.000 description 1
- LHDMWLQERSCKIB-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-piperidin-4-yloxypyridine-4-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=CN=C1OC1CCNCC1 LHDMWLQERSCKIB-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0013737.2A GB0013737D0 (en) | 2000-06-07 | 2000-06-07 | Novel compounds |
| PCT/SE2001/001257 WO2001094338A1 (en) | 2000-06-07 | 2001-06-01 | Admantane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004506611A JP2004506611A (ja) | 2004-03-04 |
| JP2004506611A5 true JP2004506611A5 (https=) | 2008-07-17 |
Family
ID=9893073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002501887A Withdrawn JP2004506611A (ja) | 2000-06-07 | 2001-06-01 | アダマンタン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6949539B2 (https=) |
| EP (1) | EP1292590B1 (https=) |
| JP (1) | JP2004506611A (https=) |
| AT (1) | ATE316083T1 (https=) |
| AU (1) | AU2001264474A1 (https=) |
| DE (1) | DE60116761T2 (https=) |
| GB (1) | GB0013737D0 (https=) |
| WO (1) | WO2001094338A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI258462B (en) | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
| WO2003042190A1 (en) * | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
| SE0103836D0 (sv) | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| FR2836618B1 (fr) * | 2002-02-28 | 2004-04-16 | Snecma Services | Instrument de projection thermique |
| SE0200920D0 (sv) * | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
| SE0300480D0 (sv) * | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| WO2004105797A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| EP1644042A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
| TW200507829A (en) * | 2003-05-29 | 2005-03-01 | Astrazeneca Ab | New combination |
| GB0312609D0 (en) * | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| KR100554155B1 (ko) * | 2003-06-09 | 2006-02-22 | 학교법인 포항공과대학교 | 금속/반도체 나노막대 이종구조를 이용한 전극 구조물 및그 제조 방법 |
| SE0302139D0 (sv) * | 2003-07-28 | 2003-07-28 | Astrazeneca Ab | Novel compounds |
| SE0302192D0 (sv) * | 2003-08-08 | 2003-08-08 | Astrazeneca Ab | Novel compounds |
| SE0302488D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
| JPWO2005107804A1 (ja) * | 2004-05-06 | 2008-03-21 | 小野薬品工業株式会社 | 呼吸器疾患治療剤 |
| US7241776B2 (en) * | 2004-08-02 | 2007-07-10 | Abbott Laboratories | Cyanoamidine P2X7 antagonists for the treatment of pain |
| SA05260265A (ar) * | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
| SE0402925D0 (sv) * | 2004-11-30 | 2004-11-30 | Astrazeneca Ab | Novel Compounds |
| EA201300152A1 (ru) | 2006-11-27 | 2013-07-30 | Х. Лундбекк А/С | Гетероариламидные производные |
| BRPI0809106A2 (pt) | 2007-03-22 | 2014-08-26 | Astrazeneca Ab | Derivados de quinolina para o tratamento de doenças inflamatórias |
| BRPI0809567A2 (pt) | 2007-04-10 | 2014-09-23 | Lundbeck & Co As H | Composto, composição farmacêutica, método para modular a atividade de um receptor de p2x7, para tratar uma condição responsiva à modulação do receptor de p2x7 em um paciente, para inibir a morte de células do gânglio retinal em um paciente, e para determinar a presença ou ausência do receptor de p2x7 em uma amostra, preparação farmacêutica acondiciaonada, e, uso de um composto |
| US8106073B2 (en) | 2007-11-30 | 2012-01-31 | Astrazeneca Ab | Quinoline derivatives 057 |
| CN102046240B (zh) | 2008-03-25 | 2014-06-25 | 阿费克蒂斯药品公司 | 新的p2x7r拮抗剂及其应用 |
| WO2010118921A1 (en) | 2009-04-14 | 2010-10-21 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| EP2569281A1 (en) | 2010-05-14 | 2013-03-20 | Affectis Pharmaceuticals AG | Novel methods for the preparation of p2x7r antagonists |
| JP2013249256A (ja) * | 2010-09-15 | 2013-12-12 | Astellas Pharma Inc | 脂肪性肝疾患治療薬 |
| WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| CN103687860B (zh) | 2011-07-22 | 2016-06-08 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
| EA024204B1 (ru) | 2012-01-20 | 2016-08-31 | Актелион Фармасьютиклз Лтд. | Производные гетероциклических амидов в качестве антагонистов p2xрецептора |
| AR093921A1 (es) | 2012-12-12 | 2015-06-24 | Actelion Pharmaceuticals Ltd | Derivados de indol carboxamida como antagonistas del receptor p2x7 |
| KR102232744B1 (ko) | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
| ES2616883T3 (es) | 2013-01-22 | 2017-06-14 | Actelion Pharmaceuticals Ltd. | Derivados amida heterocíclicos como antagonistas del receptor P2X7 |
| KR102222220B1 (ko) | 2013-01-22 | 2021-03-03 | 이도르시아 파마슈티컬스 리미티드 | Ｐ2ｘ7 수용체 길항제로서의 헤테로시클릭 아미드 유도체 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352912A (en) | 1963-07-24 | 1967-11-14 | Du Pont | Adamantanes and tricyclo[4. 3. 1. 1 3.8] undecanes |
| US3471491A (en) * | 1967-08-28 | 1969-10-07 | Squibb & Sons Inc | Adamantyl-s-triazines |
| US3464998A (en) * | 1968-03-04 | 1969-09-02 | Searle & Co | Adamantyl esters and amides of pyridinecarboxylic acids |
| GB1274652A (en) | 1968-08-27 | 1972-05-17 | Lilly Industries Ltd | Adamantanyl-alkylamine derivatives and their preparation |
| IL53441A0 (en) | 1977-11-22 | 1978-01-31 | Teva Pharma | Methyladamantyl hydrazines their preparation and pharmaceutical compositions containing them |
| US4751292A (en) * | 1985-07-02 | 1988-06-14 | The Plant Cell Research Institute, Inc. | Adamantyl purines |
| PL181782B1 (pl) | 1993-08-10 | 2001-09-28 | Black James Foundation | Nowe zwiazki i sposób wytwarzania nowych zwiazków PL |
| FR2761358B1 (fr) | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| SE9704544D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| SE9704545D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| CN1147483C (zh) | 1999-04-09 | 2004-04-28 | 阿斯特拉曾尼卡有限公司 | 金刚烷衍生物 |
| SE0103836D0 (sv) | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| SE0200920D0 (sv) | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
-
2000
- 2000-06-07 GB GBGB0013737.2A patent/GB0013737D0/en not_active Ceased
-
2001
- 2001-06-01 US US10/297,486 patent/US6949539B2/en not_active Expired - Fee Related
- 2001-06-01 JP JP2002501887A patent/JP2004506611A/ja not_active Withdrawn
- 2001-06-01 AT AT01938903T patent/ATE316083T1/de not_active IP Right Cessation
- 2001-06-01 EP EP01938903A patent/EP1292590B1/en not_active Expired - Lifetime
- 2001-06-01 AU AU2001264474A patent/AU2001264474A1/en not_active Abandoned
- 2001-06-01 DE DE60116761T patent/DE60116761T2/de not_active Expired - Fee Related
- 2001-06-01 WO PCT/SE2001/001257 patent/WO2001094338A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004506611A5 (https=) | ||
| JP4742026B2 (ja) | ロフルミラストの新規の製造方法 | |
| JP2021523225A5 (https=) | ||
| JP2005519028A5 (https=) | ||
| JP2004506611A (ja) | アダマンタン誘導体 | |
| PL207158B1 (pl) | Związek amidynowy, środek farmaceutyczny, zastosowanie tego związku i sposób jego wytwarzania | |
| HUP0200450A2 (hu) | Imidazo[4,5-b]piridinio-metil-csoportot tartalmazó cefémvegyületek, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| US20110028508A1 (en) | Novel process for the preparation of scopine esters | |
| EP1448195A1 (en) | N-adamantylmethyl derivates and intermediates as pharmaceutical compositions and processes for their preparation | |
| JP7408819B2 (ja) | イソインドリン誘導体、並びにその医薬組成物及び使用 | |
| AU2021367554B2 (en) | Deuterated hpk1 kinase inhibitor, and preparation method therefor and use thereof | |
| WO2013007184A1 (zh) | 抗肿瘤药物四氢化萘酰胺类化合物及其药学上可接受的盐及制备方法和应用 | |
| TW408117B (en) | Use of N-substituted phenothiazines | |
| JP7618642B2 (ja) | インターロイキンの調節におけるプロドラッグ | |
| AU4595393A (en) | Novel piprazine carboxamides | |
| KR101106127B1 (ko) | 다산성 염기화합물의 산부가염의 제조방법 | |
| TWI281920B (en) | Cephalosporin intermediates | |
| JP2003503488A5 (https=) | ||
| JP2022549030A (ja) | 複素環アミド化合物、その薬学的に許容される塩およびその調製方法と使用 | |
| TWI812679B (zh) | 製備可溶性鳥苷酸環化酶刺激劑之方法 | |
| EP4172146A1 (en) | Substituted n-phenylacetamides having p2x4 receptor antagonistic activity | |
| JPH045289A (ja) | アミド化合物 | |
| JP2001506282A (ja) | ２０（ｓ）―７―エチル―９―（ｎ―メチル―ｎ―フェニル）アミジノ―カンプトテシン、その誘導体、その製造及びその抗腫瘍剤としての使用 | |
| JP2026504095A (ja) | ピラゾロキナゾリン類化合物の立体異性体、重水素化誘導体及びその用途 | |
| TW201206910A (en) | Substituted N-heterocycloalkyl bipyrrolidinylphenyl amide derivatives, preparation and therapeutic use thereof |