AU2014336258B2 - Piperazine derivatives and the use thereof as medicament - Google Patents
Piperazine derivatives and the use thereof as medicament Download PDFInfo
- Publication number
- AU2014336258B2 AU2014336258B2 AU2014336258A AU2014336258A AU2014336258B2 AU 2014336258 B2 AU2014336258 B2 AU 2014336258B2 AU 2014336258 A AU2014336258 A AU 2014336258A AU 2014336258 A AU2014336258 A AU 2014336258A AU 2014336258 B2 AU2014336258 B2 AU 2014336258B2
- Authority
- AU
- Australia
- Prior art keywords
- mmol
- pct
- hplc
- instead
- title compound
- 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.)
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Links
- XYYGIKUNELJGAO-UHFFFAOYSA-N C=S(CC1)(CCC1C(N(CCN(C1)c2ncc(C(F)(F)F)cc2)C1c(ccc(F)c1)c1F)=O)=O Chemical compound C=S(CC1)(CCC1C(N(CCN(C1)c2ncc(C(F)(F)F)cc2)C1c(ccc(F)c1)c1F)=O)=O XYYGIKUNELJGAO-UHFFFAOYSA-N 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N CC1NCCNC1 Chemical compound CC1NCCNC1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- CFGGSSOAGKMRDZ-UHFFFAOYSA-N CCCNC(CC)c([s]1)ccc1I Chemical compound CCCNC(CC)c([s]1)ccc1I CFGGSSOAGKMRDZ-UHFFFAOYSA-N 0.000 description 1
- JDEUXJHEXRULIM-UHFFFAOYSA-N CNC(N(CC1)CC(c2ccc(C(F)(F)F)[s]2)N1C(C(CC1)CCS1(=O)=O)=O)=O Chemical compound CNC(N(CC1)CC(c2ccc(C(F)(F)F)[s]2)N1C(C(CC1)CCS1(=O)=O)=O)=O JDEUXJHEXRULIM-UHFFFAOYSA-N 0.000 description 1
- XRWAPVMJRIDHOM-UHFFFAOYSA-N Cc1ccc(C(CN(CC2)c3ncc(C(F)(F)F)cn3)N2C(C(CC2)CCS2(=C)=C)=O)[s]1 Chemical compound Cc1ccc(C(CN(CC2)c3ncc(C(F)(F)F)cn3)N2C(C(CC2)CCS2(=C)=C)=O)[s]1 XRWAPVMJRIDHOM-UHFFFAOYSA-N 0.000 description 1
- PCPITHHWVQQETO-UHFFFAOYSA-N Cc1cccc(C(CN(CC2)c3ncc(C)cn3)N2C(C(CC2)CCS2(=C)=C)=O)c1 Chemical compound Cc1cccc(C(CN(CC2)c3ncc(C)cn3)N2C(C(CC2)CCS2(=C)=C)=O)c1 PCPITHHWVQQETO-UHFFFAOYSA-N 0.000 description 1
- ZNEHIDGAPGVZSA-UHFFFAOYSA-N Cc1cccc(F)c1F Chemical compound Cc1cccc(F)c1F ZNEHIDGAPGVZSA-UHFFFAOYSA-N 0.000 description 1
- NWHHPUDKDYLIBY-UHFFFAOYSA-N Cc1cnc(C(CN(CC2)c3ncc(C(F)(F)F)nc3)N2C(C(CC2)CCS2(=O)=O)=O)[s]1 Chemical compound Cc1cnc(C(CN(CC2)c3ncc(C(F)(F)F)nc3)N2C(C(CC2)CCS2(=O)=O)=O)[s]1 NWHHPUDKDYLIBY-UHFFFAOYSA-N 0.000 description 1
- CEPCPXLLFXPZGW-UHFFFAOYSA-N Nc(c(F)c1)ccc1F Chemical compound Nc(c(F)c1)ccc1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N Nc(cc1)ccc1F Chemical compound Nc(cc1)ccc1F KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- AXNUZKSSQHTNPZ-UHFFFAOYSA-N Nc(cc1F)ccc1F Chemical compound Nc(cc1F)ccc1F AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N Nc1cccc(F)c1 Chemical compound Nc1cccc(F)c1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N Nc1ccccc1F Chemical compound Nc1ccccc1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- AASAPPJCMBYCII-UHFFFAOYSA-N O=C(C(CC1)CCS1(=O)=O)N(CCN(C1)c2ncc(C(F)(F)F)cc2)C1c1cc(F)ccc1 Chemical compound O=C(C(CC1)CCS1(=O)=O)N(CCN(C1)c2ncc(C(F)(F)F)cc2)C1c1cc(F)ccc1 AASAPPJCMBYCII-UHFFFAOYSA-N 0.000 description 1
- RERHJSNQDPRKIZ-UHFFFAOYSA-N O=C(C(CC1)CCS1(=O)=O)N(CCN(C1)c2ncc(C3CC3)cn2)C1c(cc1)ccc1F Chemical compound O=C(C(CC1)CCS1(=O)=O)N(CCN(C1)c2ncc(C3CC3)cn2)C1c(cc1)ccc1F RERHJSNQDPRKIZ-UHFFFAOYSA-N 0.000 description 1
- XHJOIRKFCOJNKZ-UHFFFAOYSA-N O=C(C(CC1)CCS1(=O)=O)N(CCN(C1)c2ncccc2)C1c(ccc(F)c1)c1F Chemical compound O=C(C(CC1)CCS1(=O)=O)N(CCN(C1)c2ncccc2)C1c(ccc(F)c1)c1F XHJOIRKFCOJNKZ-UHFFFAOYSA-N 0.000 description 1
- NJEBMFGKHBWDEA-UHFFFAOYSA-N O=C(C(CC1)CCS1(=O)=O)N(CCNC1)C1c(cccc1F)c1F Chemical compound O=C(C(CC1)CCS1(=O)=O)N(CCNC1)C1c(cccc1F)c1F NJEBMFGKHBWDEA-UHFFFAOYSA-N 0.000 description 1
- WXLXTBFCCKRYNK-UHFFFAOYSA-N O=C(C(CC1)CCS1(=O)=O)N(CCNC1)C1c1ccccc1 Chemical compound O=C(C(CC1)CCS1(=O)=O)N(CCNC1)C1c1ccccc1 WXLXTBFCCKRYNK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13188904 | 2013-10-16 | ||
| EP13188904.0 | 2013-10-16 | ||
| PCT/EP2014/072085 WO2015055698A1 (en) | 2013-10-16 | 2014-10-15 | Piperazine derivatives and the use thereof as medicament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014336258A1 AU2014336258A1 (en) | 2016-04-14 |
| AU2014336258B2 true AU2014336258B2 (en) | 2018-07-12 |
Family
ID=49354583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014336258A Active AU2014336258B2 (en) | 2013-10-16 | 2014-10-15 | Piperazine derivatives and the use thereof as medicament |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9233953B2 (enExample) |
| EP (1) | EP3057963B1 (enExample) |
| JP (1) | JP6483105B2 (enExample) |
| KR (1) | KR102281284B1 (enExample) |
| CN (1) | CN105636961B (enExample) |
| AR (1) | AR098037A1 (enExample) |
| AU (1) | AU2014336258B2 (enExample) |
| BR (1) | BR112016008062B1 (enExample) |
| CA (1) | CA2926754C (enExample) |
| CL (1) | CL2016000884A1 (enExample) |
| DK (1) | DK3057963T3 (enExample) |
| EA (1) | EA029313B1 (enExample) |
| ES (1) | ES2745555T3 (enExample) |
| HU (1) | HUE047044T2 (enExample) |
| IL (1) | IL244693B (enExample) |
| MX (1) | MX370006B (enExample) |
| PH (1) | PH12016500577B1 (enExample) |
| PL (1) | PL3057963T3 (enExample) |
| TW (1) | TW201609716A (enExample) |
| UY (1) | UY35785A (enExample) |
| WO (1) | WO2015055698A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106854189A (zh) * | 2015-12-08 | 2017-06-16 | 湖南华腾制药有限公司 | 一种哌嗪化合物的合成方法 |
| CN107778257A (zh) * | 2016-08-29 | 2018-03-09 | 湖南华腾制药有限公司 | 一种哌嗪衍生物的合成方法 |
| CN106977463A (zh) * | 2017-05-31 | 2017-07-25 | 湖南华腾制药有限公司 | 一种联苯取代哌嗪衍生物的合成方法 |
| CN107417679A (zh) * | 2017-08-04 | 2017-12-01 | 河南农业大学 | 1,3‑唑类取代吡嗪类化合物的制备方法 |
| WO2021142329A1 (en) | 2020-01-09 | 2021-07-15 | Disc Medicine, Inc. | Methods of treating erythropoietic protoporphyria, x-linked protoporphyria, or congenital erythropoietic porphyria with glycine transport inhibitors |
| CN117050051A (zh) * | 2023-08-14 | 2023-11-14 | 上海药坦药物研究开发有限公司 | 一种2-溴-1-（5-碘噻吩-2-基）-乙酮的纯化方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004035556A1 (en) * | 2002-10-16 | 2004-04-29 | Glaxo Group Limited | Substituted piperazines, (1,4) diaszepines, and 2,5-diazabicyclo (2.2.1) heptanes as histamine h1 and/or h3 antagonists or histamine h3 reverse antagonists |
| WO2006094840A1 (en) * | 2005-03-11 | 2006-09-14 | Glaxo Group Limited | Compounds |
| WO2006113704A2 (en) * | 2005-04-18 | 2006-10-26 | Neurogen Corporation | Subtituted heteroaryl cb1 antagonists |
| WO2011003418A1 (en) * | 2009-07-08 | 2011-01-13 | Leo Pharma A/S | Heterocyclic compounds as jak receptor and protein tyrosine kinase inhibitors |
-
2014
- 2014-10-14 US US14/513,918 patent/US9233953B2/en active Active
- 2014-10-15 CA CA2926754A patent/CA2926754C/en active Active
- 2014-10-15 KR KR1020167012860A patent/KR102281284B1/ko active Active
- 2014-10-15 HU HUE14784235A patent/HUE047044T2/hu unknown
- 2014-10-15 AR ARP140103834A patent/AR098037A1/es unknown
- 2014-10-15 EA EA201600323A patent/EA029313B1/ru not_active IP Right Cessation
- 2014-10-15 TW TW103135739A patent/TW201609716A/zh unknown
- 2014-10-15 DK DK14784235.5T patent/DK3057963T3/da active
- 2014-10-15 MX MX2016004847A patent/MX370006B/es active IP Right Grant
- 2014-10-15 ES ES14784235T patent/ES2745555T3/es active Active
- 2014-10-15 PL PL14784235T patent/PL3057963T3/pl unknown
- 2014-10-15 AU AU2014336258A patent/AU2014336258B2/en active Active
- 2014-10-15 JP JP2016523968A patent/JP6483105B2/ja active Active
- 2014-10-15 BR BR112016008062-9A patent/BR112016008062B1/pt active IP Right Grant
- 2014-10-15 WO PCT/EP2014/072085 patent/WO2015055698A1/en not_active Ceased
- 2014-10-15 EP EP14784235.5A patent/EP3057963B1/en active Active
- 2014-10-15 CN CN201480056368.8A patent/CN105636961B/zh active Active
- 2014-10-16 UY UY0001035785A patent/UY35785A/es unknown
-
2016
- 2016-03-21 IL IL244693A patent/IL244693B/en active IP Right Grant
- 2016-03-30 PH PH12016500577A patent/PH12016500577B1/en unknown
- 2016-04-14 CL CL2016000884A patent/CL2016000884A1/es unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004035556A1 (en) * | 2002-10-16 | 2004-04-29 | Glaxo Group Limited | Substituted piperazines, (1,4) diaszepines, and 2,5-diazabicyclo (2.2.1) heptanes as histamine h1 and/or h3 antagonists or histamine h3 reverse antagonists |
| WO2006094840A1 (en) * | 2005-03-11 | 2006-09-14 | Glaxo Group Limited | Compounds |
| WO2006113704A2 (en) * | 2005-04-18 | 2006-10-26 | Neurogen Corporation | Subtituted heteroaryl cb1 antagonists |
| WO2011003418A1 (en) * | 2009-07-08 | 2011-01-13 | Leo Pharma A/S | Heterocyclic compounds as jak receptor and protein tyrosine kinase inhibitors |
Non-Patent Citations (4)
| Title |
|---|
| Bitopertin, from Wikipedia, 1 page, retrieved from "http://en.wikipedia.org/w/index.php?title=Bitopertin&oldid=643636360", Feb. 8, 2015 * |
| E. PINARD ET AL, JOURNAL OF MEDICINAL CHEMISTRY, 2010, vol. 53, pages 4603 - 4614 * |
| Harada et al.European Journal of Phatmacology, vol. 685, pp. 59-69 (2012) * |
| Harvey et al. Nature Reviews/Drug Discovery vol. 12 pp. 866-885 (2013) * |
Also Published As
| Publication number | Publication date |
|---|---|
| UY35785A (es) | 2015-04-30 |
| ES2745555T3 (es) | 2020-03-02 |
| BR112016008062A2 (enExample) | 2017-08-01 |
| HUE047044T2 (hu) | 2020-04-28 |
| NZ718251A (en) | 2021-02-26 |
| MX370006B (es) | 2019-11-28 |
| DK3057963T3 (da) | 2019-09-16 |
| PH12016500577A1 (en) | 2016-06-20 |
| US9233953B2 (en) | 2016-01-12 |
| EA029313B1 (ru) | 2018-03-30 |
| AR098037A1 (es) | 2016-04-27 |
| CN105636961A (zh) | 2016-06-01 |
| BR112016008062B1 (pt) | 2022-11-16 |
| EP3057963B1 (en) | 2019-06-19 |
| CL2016000884A1 (es) | 2016-12-30 |
| KR20160062187A (ko) | 2016-06-01 |
| CA2926754A1 (en) | 2015-04-23 |
| TW201609716A (zh) | 2016-03-16 |
| IL244693B (en) | 2019-08-29 |
| JP6483105B2 (ja) | 2019-03-13 |
| EP3057963A1 (en) | 2016-08-24 |
| US20150105397A1 (en) | 2015-04-16 |
| JP2016533368A (ja) | 2016-10-27 |
| MX2016004847A (es) | 2016-07-19 |
| WO2015055698A1 (en) | 2015-04-23 |
| KR102281284B1 (ko) | 2021-07-23 |
| CA2926754C (en) | 2021-09-14 |
| PL3057963T3 (pl) | 2019-12-31 |
| PH12016500577B1 (en) | 2016-06-20 |
| EA201600323A1 (ru) | 2016-10-31 |
| AU2014336258A1 (en) | 2016-04-14 |
| CN105636961B (zh) | 2019-11-05 |
| IL244693A0 (en) | 2016-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |