RU2013156864A - Способ получения дейтерированных соединений, содержащих n-алкильные группы - Google Patents
Способ получения дейтерированных соединений, содержащих n-алкильные группы Download PDFInfo
- Publication number
- RU2013156864A RU2013156864A RU2013156864/04A RU2013156864A RU2013156864A RU 2013156864 A RU2013156864 A RU 2013156864A RU 2013156864/04 A RU2013156864/04 A RU 2013156864/04A RU 2013156864 A RU2013156864 A RU 2013156864A RU 2013156864 A RU2013156864 A RU 2013156864A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- phenyl
- alkylene
- bond
- optionally substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 15
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract 5
- 229910052805 deuterium Inorganic materials 0.000 claims abstract 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 239000003054 catalyst Substances 0.000 claims abstract 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 25
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 2
- -1 cyano, hydroxyl Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 1
- XXRCBURMZUPAJF-UHFFFAOYSA-N 2-[2-(1-hydroxy-2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-yl)phenyl]-3,4,5-triphenylcyclopenta-2,4-dien-1-one Chemical group OC1(C(=C(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=C(C=CC=C1)C=1C(C(=C(C=1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)=O XXRCBURMZUPAJF-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/08—Monoamines containing alkyl groups having a different number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D211/14—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 with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrrole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11305634.5 | 2011-05-23 | ||
| EP11305634 | 2011-05-23 | ||
| PCT/EP2012/059344 WO2012160015A1 (en) | 2011-05-23 | 2012-05-21 | Process for the preparation of deuterated compounds containing n-alkyl groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2013156864A true RU2013156864A (ru) | 2015-06-27 |
Family
ID=46146876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013156864/04A RU2013156864A (ru) | 2011-05-23 | 2012-05-21 | Способ получения дейтерированных соединений, содержащих n-алкильные группы |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9340489B2 (https=) |
| EP (1) | EP2714624B1 (https=) |
| JP (1) | JP5925301B2 (https=) |
| KR (1) | KR20140030267A (https=) |
| CN (1) | CN103702961A (https=) |
| CA (1) | CA2834920A1 (https=) |
| IL (1) | IL229037A0 (https=) |
| RU (1) | RU2013156864A (https=) |
| SG (1) | SG194625A1 (https=) |
| WO (1) | WO2012160015A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX387055B (es) | 2014-06-06 | 2025-03-19 | Res Triangle Inst | Agonistas del receptor de apelina (apj) y usos de los mismos. |
| EP3218373B1 (en) * | 2014-11-10 | 2020-07-22 | Evrys Bio, LLC | Anti-hcmv compositions and methods |
| WO2017100558A1 (en) | 2015-12-09 | 2017-06-15 | Research Triangle Institute | Improved apelin receptor (apj) agonists and uses thereof |
| JP7048572B6 (ja) | 2016-09-16 | 2023-12-20 | リサーチ トライアングル インスティテュート | テトラヒドロイソキノリンカッパーオピオイドアンタゴニスト |
| MX394907B (es) | 2016-10-12 | 2025-03-24 | Res Triangle Inst | Agonistas heterociclicos del receptor de apelina (apj) y usos de los mismos |
| JOP20190072A1 (ar) | 2016-10-13 | 2019-04-07 | Glaxosmithkline Ip Dev Ltd | مشتقات 1، 3 سيكلوبوتان ثنائي الاستبدال أو آزيتيدين كمثبطات للإنزيم المخلق للبروستاجلاندين d المكون للدم |
| CA3036382A1 (en) | 2016-12-21 | 2018-06-28 | Research Triangle Institute | Diaryl purine derivatives with improved bioavailability |
| CA3059585A1 (en) | 2017-04-27 | 2018-11-01 | Deuteria Beverages, Llc | Process for the preparation of deuterated ethanol from d2o |
| AU2018260728B2 (en) * | 2017-04-27 | 2022-07-21 | Deuteria Beverages, Llc | Process for the preparation of deuterated ethanol from D2 |
| AU2018346597B2 (en) | 2017-10-06 | 2023-07-13 | Forma Therapeutics, Inc. | Inhibiting Ubiquitin Specific Peptidase 30 |
| CN109748767A (zh) * | 2017-11-07 | 2019-05-14 | 朱允涛 | 一种利用微波反应装置制备氘代胺类化合物的方法 |
| JP7449242B2 (ja) | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的ペプチダーゼ３０（ｕｓｐ３０）阻害剤として有用な縮合二環化合物 |
| CA3109809A1 (en) | 2018-08-20 | 2020-02-27 | Duke University | Methods and compositions for drugs to treat ophthalmic diseases |
| JP7530889B2 (ja) | 2018-10-05 | 2024-08-08 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的プロテアーゼ３０（ｕｓｐ３０）阻害剤として作用する縮合ピロリン |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| SG11202106692UA (en) * | 2018-12-21 | 2021-07-29 | Concert Pharmaceuticals Inc | Deuterated forms and derivatives of volinanserin |
| US12441707B2 (en) | 2019-12-30 | 2025-10-14 | Tyra Biosciences, Inc. | Indazole compounds |
| KR20230152654A (ko) | 2020-12-30 | 2023-11-03 | 타이라 바이오사이언시스, 인크. | 키나아제 억제제로서의 인다졸 화합물 |
| WO2022182547A1 (en) | 2021-02-25 | 2022-09-01 | Research Triangle Institute | Heteroaryl derivatives as apelin receptor agonists |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4254129A (en) | 1979-04-10 | 1981-03-03 | Richardson-Merrell Inc. | Piperidine derivatives |
| WO1989001342A2 (en) * | 1987-08-07 | 1989-02-23 | Mallinckrodt, Inc. | Diagnostic or radiotherapeutic composition comprising a hydrogen containing compound |
| US5075337A (en) * | 1989-07-26 | 1991-12-24 | G. D. Searle & Co. | Alpha-deuterated 2-alkylaminoacetamide derivatives having reduced toxicity for treatment of CNS disorders |
| CA2083698C (en) | 1990-06-01 | 1997-11-04 | Albert A. Carr | (+)-alpha-(2,3-dimethoxyphenyl)-1- [2-(4-fluorophenyl) ethyl]-4-piperidinemethanol |
| ES2293638T3 (es) | 1994-03-25 | 2008-03-16 | Isotechnika, Inc. | Mejora de la eficacia de farmacos por deuteracion. |
| JP4497815B2 (ja) | 2001-02-16 | 2010-07-07 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 新規な複素環式アミド誘導体およびドーパミンｄ３受容体リガンドとしてのその使用 |
| TW200413273A (en) | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| TW200413274A (en) * | 2002-12-27 | 2004-08-01 | Wako Pure Chem Ind Ltd | Deuteration or tritiation method |
| KR20060129284A (ko) * | 2004-01-23 | 2006-12-15 | 와코 쥰야꾸 고교 가부시키가이샤 | 혼합촉매를 사용한 중수소화방법 |
| CA2701638A1 (en) * | 2007-04-02 | 2008-10-09 | Concert Pharmaceuticals Inc. | Pharmaceutical calcimimetics |
| JP5454140B2 (ja) * | 2007-07-05 | 2014-03-26 | 和光純薬工業株式会社 | ルテニウム触媒を用いた重水素化方法 |
| US20100143287A1 (en) * | 2008-12-09 | 2010-06-10 | Auspex Pharmaceuticals, Inc. | Trifluoromethylphenyl modulators of calcium-sensing receptor |
-
2012
- 2012-05-21 SG SG2013079298A patent/SG194625A1/en unknown
- 2012-05-21 WO PCT/EP2012/059344 patent/WO2012160015A1/en not_active Ceased
- 2012-05-21 KR KR1020137034057A patent/KR20140030267A/ko not_active Withdrawn
- 2012-05-21 EP EP12722367.5A patent/EP2714624B1/en not_active Not-in-force
- 2012-05-21 CA CA2834920A patent/CA2834920A1/en not_active Abandoned
- 2012-05-21 US US14/118,705 patent/US9340489B2/en not_active Expired - Fee Related
- 2012-05-21 CN CN201280036588.5A patent/CN103702961A/zh active Pending
- 2012-05-21 JP JP2014511830A patent/JP5925301B2/ja not_active Expired - Fee Related
- 2012-05-21 RU RU2013156864/04A patent/RU2013156864A/ru not_active Application Discontinuation
-
2013
- 2013-10-23 IL IL229037A patent/IL229037A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2014524888A (ja) | 2014-09-25 |
| US20140081019A1 (en) | 2014-03-20 |
| EP2714624A1 (en) | 2014-04-09 |
| IL229037A0 (en) | 2013-12-31 |
| SG194625A1 (en) | 2013-12-30 |
| CN103702961A (zh) | 2014-04-02 |
| JP5925301B2 (ja) | 2016-05-25 |
| KR20140030267A (ko) | 2014-03-11 |
| WO2012160015A1 (en) | 2012-11-29 |
| EP2714624B1 (en) | 2017-12-27 |
| US9340489B2 (en) | 2016-05-17 |
| CA2834920A1 (en) | 2012-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20150522 |