JP2011201916A5 - - Google Patents
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- Publication number
- JP2011201916A5 JP2011201916A5 JP2011128516A JP2011128516A JP2011201916A5 JP 2011201916 A5 JP2011201916 A5 JP 2011201916A5 JP 2011128516 A JP2011128516 A JP 2011128516A JP 2011128516 A JP2011128516 A JP 2011128516A JP 2011201916 A5 JP2011201916 A5 JP 2011201916A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazine
- pyridyl
- piperidinyl
- dihydro
- methyl
- 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
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- 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 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 208000019553 vascular disease Diseases 0.000 description 8
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- -1 1-piperidyl Chemical group 0.000 description 3
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- FSVCQIDHPKZJSO-UHFFFAOYSA-L nitro blue tetrazolium dichloride Chemical compound [Cl-].[Cl-].COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 FSVCQIDHPKZJSO-UHFFFAOYSA-L 0.000 description 3
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
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- 229920001592 potato starch Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 230000010410 reperfusion Effects 0.000 description 2
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- FGZWBZVLFVMHFY-UHFFFAOYSA-N 3-pyridin-3-yl-2h-1,2,4-oxadiazine Chemical compound N1C=CON=C1C1=CC=CN=C1 FGZWBZVLFVMHFY-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- MVLOQULXIYSERZ-UHFFFAOYSA-N n'-(2-hydroxy-3-piperidin-1-ylpropoxy)pyridine-3-carboximidamide Chemical compound C1CCCCN1CC(O)CONC(=N)C1=CC=CN=C1 MVLOQULXIYSERZ-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP9802897 | 1998-12-14 | ||
| HU9802897A HU226617B1 (en) | 1998-12-14 | 1998-12-14 | Optically active pyridyl-4h-1,2,4-oxadiazine derivatives, and pharmaceutical composition containing the compound as active ingredient |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000588174A Division JP2002532498A (ja) | 1998-12-14 | 1999-12-07 | 光学活性ピリジル−４ｈ−１，２，４−オキサジアジン誘導体およびその血管疾患の治療における使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011201916A JP2011201916A (ja) | 2011-10-13 |
| JP2011201916A5 true JP2011201916A5 (OSRAM) | 2012-08-02 |
| JP5620340B2 JP5620340B2 (ja) | 2014-11-05 |
Family
ID=10991166
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000588174A Withdrawn JP2002532498A (ja) | 1998-12-14 | 1999-12-07 | 光学活性ピリジル−４ｈ−１，２，４−オキサジアジン誘導体およびその血管疾患の治療における使用 |
| JP2011128516A Expired - Lifetime JP5620340B2 (ja) | 1998-12-14 | 2011-06-08 | 光学活性ピリジル−４ｈ−１，２，４−オキサジアジン誘導体およびその血管疾患の治療における使用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000588174A Withdrawn JP2002532498A (ja) | 1998-12-14 | 1999-12-07 | 光学活性ピリジル−４ｈ−１，２，４−オキサジアジン誘導体およびその血管疾患の治療における使用 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6384029B1 (OSRAM) |
| EP (1) | EP1147105B1 (OSRAM) |
| JP (2) | JP2002532498A (OSRAM) |
| KR (1) | KR100661774B1 (OSRAM) |
| AT (1) | ATE266027T1 (OSRAM) |
| AU (1) | AU765336B2 (OSRAM) |
| BG (1) | BG65179B1 (OSRAM) |
| BR (1) | BR9913982A (OSRAM) |
| CA (1) | CA2340734C (OSRAM) |
| CZ (1) | CZ300764B6 (OSRAM) |
| DE (1) | DE69917074T2 (OSRAM) |
| DK (1) | DK1147105T3 (OSRAM) |
| EE (1) | EE04551B1 (OSRAM) |
| ES (1) | ES2219091T3 (OSRAM) |
| HR (1) | HRP20010133B1 (OSRAM) |
| HU (1) | HU226617B1 (OSRAM) |
| IL (1) | IL141515A (OSRAM) |
| NO (1) | NO317649B1 (OSRAM) |
| PL (1) | PL196584B1 (OSRAM) |
| PT (1) | PT1147105E (OSRAM) |
| RS (1) | RS50129B (OSRAM) |
| RU (1) | RU2222538C2 (OSRAM) |
| SI (1) | SI1147105T1 (OSRAM) |
| SK (1) | SK285582B6 (OSRAM) |
| UA (1) | UA70340C2 (OSRAM) |
| WO (1) | WO2000035914A1 (OSRAM) |
| ZA (1) | ZA200101182B (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL371251A1 (en) | 2002-01-11 | 2005-06-13 | Biorex Kutato Es Fejlesztö Rt. | Carboxamidine derivatives and their use in the treatment of vascular diseases |
| KR100678577B1 (ko) * | 2006-09-11 | 2007-02-06 | 조만규 | 가정용 분전함 |
| ES2963910T3 (es) | 2008-06-26 | 2024-04-03 | Zevra Denmark As | Uso de Hsp70 como regulador de la actividad enzimática |
| CA2743782A1 (en) | 2008-11-18 | 2010-05-27 | Santen Pharmaceutical Co., Ltd. | Therapeutic agent for chorioretinal degenerative disease containing pyridine-3-carbaldehyde o-(piperidin-1-yl-propyl)-oxime derivative as active ingredient |
| PT2646044T (pt) | 2010-11-30 | 2019-11-12 | Orphazyme As | Métodos para aumentar a atividade intracelular de hsp70 |
| HUP1100534A2 (en) | 2011-09-26 | 2013-04-29 | Balazs Dr Hazay | Pharmaceutical composition for the treatment of muscle atrophy |
| HUE054957T2 (hu) | 2014-09-15 | 2021-10-28 | Orphazyme As | Arimoklomol készítése |
| US10898476B2 (en) | 2016-04-13 | 2021-01-26 | Orphazyme A/S | Heat shock proteins and cholesterol homeostasis |
| RU2021117465A (ru) | 2016-04-29 | 2021-07-22 | Орфазим А/С | Аримокломол для лечения ассоциированных с глюкоцереброзидазой нарушений |
| WO2018215597A1 (en) | 2017-05-24 | 2018-11-29 | Orphazyme A/S | Heat shock protein inducers and frontotemporal disorders |
| BR112020024182A2 (pt) | 2018-05-28 | 2021-03-30 | Orphazyme A/S | Métodos para detectar proteína de choque térmico 70, para diagnosticar uma doença apresentando um nível reduzido de proteína de choque térmico 70, para selecionar um paciente tendo uma doença apresentando um nível reduzido de hsp70, para monitorar progressão de doença em um indivíduo, para monitorar a eficácia de uma terapia para tratamento de uma doença, e, para ajustar a dosagem de um derivado de hidroxilamina de molécula pequena. |
| IL303026A (en) | 2020-11-19 | 2023-07-01 | Zevra Denmark As | Processes for preparing arimoclomol citrate and intermediates thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT395853B (de) * | 1991-01-31 | 1993-03-25 | Chem Pharm Forsch Gmbh | Neue imidazolderivate, verfahren zu ihrer herstellung und ihre verwendung |
| HU222994B1 (hu) * | 1995-11-02 | 2004-01-28 | BIOREX Kutató és Fejlesztő Rt. | Hidroxilaminszármazékok és azok alkalmazása sejtek molekuláris chaperon-termelésének fokozására alkalmas gyógyszerkészítmények előállítására |
| WO1997016349A1 (en) * | 1995-11-03 | 1997-05-09 | Global Trading Uk Limited | Apparatus for dispensing and filling bags at a checkout counter of a supermarket |
| UA64716C2 (en) * | 1996-08-09 | 2004-03-15 | Pharmaceuticals for therapy or prevention of illnesses connected with dysfunction of vascular endothelial cells |
-
1998
- 1998-12-14 HU HU9802897A patent/HU226617B1/hu not_active IP Right Cessation
-
1999
- 1999-07-12 UA UA2001063850A patent/UA70340C2/uk unknown
- 1999-12-07 AU AU17906/00A patent/AU765336B2/en not_active Expired
- 1999-12-07 IL IL14151599A patent/IL141515A/xx not_active IP Right Cessation
- 1999-12-07 AT AT99961225T patent/ATE266027T1/de active
- 1999-12-07 SI SI9930566T patent/SI1147105T1/xx unknown
- 1999-12-07 HR HR20010133A patent/HRP20010133B1/xx not_active IP Right Cessation
- 1999-12-07 RS YUP-250/01A patent/RS50129B/sr unknown
- 1999-12-07 PL PL346767A patent/PL196584B1/pl not_active IP Right Cessation
- 1999-12-07 CA CA002340734A patent/CA2340734C/en not_active Expired - Lifetime
- 1999-12-07 DK DK99961225T patent/DK1147105T3/da active
- 1999-12-07 WO PCT/HU1999/000095 patent/WO2000035914A1/en not_active Ceased
- 1999-12-07 BR BR9913982-0A patent/BR9913982A/pt not_active Application Discontinuation
- 1999-12-07 DE DE69917074T patent/DE69917074T2/de not_active Expired - Lifetime
- 1999-12-07 PT PT99961225T patent/PT1147105E/pt unknown
- 1999-12-07 EE EEP200100188A patent/EE04551B1/xx not_active IP Right Cessation
- 1999-12-07 JP JP2000588174A patent/JP2002532498A/ja not_active Withdrawn
- 1999-12-07 CZ CZ20011550A patent/CZ300764B6/cs not_active IP Right Cessation
- 1999-12-07 EP EP99961225A patent/EP1147105B1/en not_active Expired - Lifetime
- 1999-12-07 RU RU2001118854/04A patent/RU2222538C2/ru not_active IP Right Cessation
- 1999-12-07 SK SK234-2001A patent/SK285582B6/sk not_active IP Right Cessation
- 1999-12-07 ES ES99961225T patent/ES2219091T3/es not_active Expired - Lifetime
- 1999-12-07 KR KR1020017002870A patent/KR100661774B1/ko not_active Expired - Fee Related
- 1999-12-07 US US09/762,949 patent/US6384029B1/en not_active Expired - Lifetime
-
2001
- 2001-02-12 ZA ZA200101182A patent/ZA200101182B/en unknown
- 2001-03-14 BG BG105342A patent/BG65179B1/bg unknown
- 2001-05-10 NO NO20012310A patent/NO317649B1/no not_active IP Right Cessation
-
2011
- 2011-06-08 JP JP2011128516A patent/JP5620340B2/ja not_active Expired - Lifetime
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