CA2247265A1 - Process for preparing 1,4,7,10-tetraazacyclododecane and its derivatives - Google Patents
Process for preparing 1,4,7,10-tetraazacyclododecane and its derivativesInfo
- Publication number
- CA2247265A1 CA2247265A1 CA002247265A CA2247265A CA2247265A1 CA 2247265 A1 CA2247265 A1 CA 2247265A1 CA 002247265 A CA002247265 A CA 002247265A CA 2247265 A CA2247265 A CA 2247265A CA 2247265 A1 CA2247265 A1 CA 2247265A1
- Authority
- CA
- Canada
- Prior art keywords
- tetraazacyclododecane
- derivatives
- preparing
- cyclotetramerization
- benzylaziridine
- 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
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- CASDNPHWJOQUQX-UHFFFAOYSA-N 1-benzylaziridine Chemical compound C=1C=CC=CC=1CN1CC1 CASDNPHWJOQUQX-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical compound C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 abstract 1
- RRBYUSWBLVXTQN-VZCHMASFSA-N tricyclene Natural products C([C@@H]12)C3C[C@H]1C2(C)C3(C)C RRBYUSWBLVXTQN-VZCHMASFSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention concerns a process for preparing 1,4,7,10-tetraazacyclododecane (cyclene) and its derivatives on an industrial scale by the cyclotetramerization of benzylaziridine prepared in situ.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19608307.9 | 1996-02-26 | ||
| DE19608307A DE19608307C1 (en) | 1996-02-26 | 1996-02-26 | Process for the preparation of 1,4,7,10-tetraazacyclododecane and its derivatives |
| PCT/EP1997/000927 WO1997031905A1 (en) | 1996-02-26 | 1997-02-26 | Process for preparing 1,4,7,10-tetraazacyclododecane and its derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2247265A1 true CA2247265A1 (en) | 1997-09-04 |
| CA2247265C CA2247265C (en) | 2005-06-21 |
Family
ID=7787168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002247265A Expired - Lifetime CA2247265C (en) | 1996-02-26 | 1997-02-26 | Process for preparing 1,4,7,10-tetraazacyclododecane and its derivatives |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0883610B1 (en) |
| JP (2) | JP4745469B2 (en) |
| KR (1) | KR100453668B1 (en) |
| CN (1) | CN1081186C (en) |
| AT (1) | ATE194602T1 (en) |
| AU (1) | AU717720B2 (en) |
| CA (1) | CA2247265C (en) |
| CZ (1) | CZ290128B6 (en) |
| DE (2) | DE19608307C1 (en) |
| DK (1) | DK0883610T3 (en) |
| ES (1) | ES2148837T3 (en) |
| GR (1) | GR3034468T3 (en) |
| IL (1) | IL125419A (en) |
| NO (1) | NO310870B1 (en) |
| NZ (1) | NZ331520A (en) |
| PL (1) | PL185927B1 (en) |
| PT (1) | PT883610E (en) |
| SK (1) | SK281972B6 (en) |
| WO (1) | WO1997031905A1 (en) |
| ZA (1) | ZA971672B (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19608307C1 (en) * | 1996-02-26 | 1997-08-28 | Schering Ag | Process for the preparation of 1,4,7,10-tetraazacyclododecane and its derivatives |
| CZ297577B6 (en) * | 2005-10-17 | 2007-01-10 | Azacycles S. R. O. | Process for preparing 1,4,7,10-tetraazacyclododecane and N-acyl derivatives thereof |
| DE102009057274B4 (en) | 2009-12-02 | 2011-09-01 | Bayer Schering Pharma Aktiengesellschaft | Gadobutrol preparation using trioxobicyclo-octane |
| DE102010013833A1 (en) | 2010-03-29 | 2011-09-29 | Bayer Schering Pharma Aktiengesellschaft | Producing gadolinium complex of N-(hydroxymethyl-dihydroxypropyl)-triscarboxymethyl-tetraazacyclododecane useful as magnetic resonance imaging contrast agent, comprises e.g. reacting cyclic compound with dimethylformamide dimethylacetal |
| CN101845112B (en) * | 2010-06-02 | 2011-09-14 | 华东理工大学 | Preparation method of high-flexibility nuclear magnetic resonance imaging contrast agents based on high molecular nanometer particles |
| DE102010023105A1 (en) | 2010-06-04 | 2011-12-08 | Bayer Schering Pharma Aktiengesellschaft | Gadobutrol preparation in a one-pot process using DMF-acetal and N-methylimidazole |
| PT2896405T (en) | 2011-04-21 | 2020-03-31 | Bayer Ip Gmbh | Preparation of high-purity gadobutrol |
| KR102067551B1 (en) * | 2018-04-12 | 2020-01-17 | (주) 에프엔지리서치 | Compounds for remediating the contaminated soil or water |
| CN108794417A (en) * | 2018-08-04 | 2018-11-13 | 许昌恒生制药有限公司 | A kind of preparation method of medical diagnosis contrast agent intermediate |
| EP4335461A1 (en) | 2022-09-09 | 2024-03-13 | Bayer AG | Combinations of contrast agents |
| EP4335840A1 (en) | 2022-09-09 | 2024-03-13 | Bayer Aktiengesellschaft | New contrast agents for use in diagnostic imaging |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3828023A (en) * | 1971-09-13 | 1974-08-06 | Dow Chemical Co | Process for preparing cyclic oligomers of n-substituted aziridines |
| US6693190B1 (en) * | 1994-05-11 | 2004-02-17 | Bracco International B.V. | Enhanced relaxivity monomeric and multimeric compounds |
| EP0813523A2 (en) * | 1995-03-10 | 1997-12-29 | Nycomed Salutar, Inc. | Preparation of n-arylmethyl aziridine derivatives, 1,4,7,10-tetraazacyclododecane derivatives obtained therefrom and n-arylmethyl-ethanol-amine sulphonate esters as intermediates |
| DE19608307C1 (en) * | 1996-02-26 | 1997-08-28 | Schering Ag | Process for the preparation of 1,4,7,10-tetraazacyclododecane and its derivatives |
-
1996
- 1996-02-26 DE DE19608307A patent/DE19608307C1/en not_active Expired - Fee Related
-
1997
- 1997-02-26 AU AU18772/97A patent/AU717720B2/en not_active Expired
- 1997-02-26 PL PL97328468A patent/PL185927B1/en unknown
- 1997-02-26 DE DE59702009T patent/DE59702009D1/en not_active Expired - Lifetime
- 1997-02-26 WO PCT/EP1997/000927 patent/WO1997031905A1/en not_active Ceased
- 1997-02-26 SK SK1172-98A patent/SK281972B6/en not_active IP Right Cessation
- 1997-02-26 PT PT96946361T patent/PT883610E/en unknown
- 1997-02-26 DK DK96946361T patent/DK0883610T3/en active
- 1997-02-26 NZ NZ331520A patent/NZ331520A/en not_active IP Right Cessation
- 1997-02-26 CA CA002247265A patent/CA2247265C/en not_active Expired - Lifetime
- 1997-02-26 CZ CZ19982721A patent/CZ290128B6/en not_active IP Right Cessation
- 1997-02-26 AT AT96946361T patent/ATE194602T1/en active
- 1997-02-26 JP JP53059297A patent/JP4745469B2/en not_active Expired - Lifetime
- 1997-02-26 KR KR10-1998-0706649A patent/KR100453668B1/en not_active Expired - Lifetime
- 1997-02-26 IL IL12541997A patent/IL125419A/en not_active IP Right Cessation
- 1997-02-26 EP EP96946361A patent/EP0883610B1/en not_active Expired - Lifetime
- 1997-02-26 ZA ZA9701672A patent/ZA971672B/en unknown
- 1997-02-26 ES ES96946361T patent/ES2148837T3/en not_active Expired - Lifetime
- 1997-02-26 CN CN97192459A patent/CN1081186C/en not_active Expired - Lifetime
-
1998
- 1998-08-25 NO NO19983901A patent/NO310870B1/en not_active IP Right Cessation
-
2000
- 2000-09-21 GR GR20000402157T patent/GR3034468T3/en unknown
-
2009
- 2009-05-27 JP JP2009127490A patent/JP2009185077A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU1877297A (en) | 1997-09-16 |
| JP4745469B2 (en) | 2011-08-10 |
| CA2247265C (en) | 2005-06-21 |
| NO983901L (en) | 1998-08-25 |
| ES2148837T3 (en) | 2000-10-16 |
| HK1018618A1 (en) | 1999-12-30 |
| CZ272198A3 (en) | 2000-02-16 |
| DE59702009D1 (en) | 2000-08-17 |
| JP2000505467A (en) | 2000-05-09 |
| WO1997031905A1 (en) | 1997-09-04 |
| EP0883610A1 (en) | 1998-12-16 |
| PL185927B1 (en) | 2003-09-30 |
| SK117298A3 (en) | 1999-01-11 |
| CZ290128B6 (en) | 2002-06-12 |
| PL328468A1 (en) | 1999-02-01 |
| CN1081186C (en) | 2002-03-20 |
| KR19990087248A (en) | 1999-12-15 |
| SK281972B6 (en) | 2001-09-11 |
| EP0883610B1 (en) | 2000-07-12 |
| GR3034468T3 (en) | 2000-12-29 |
| IL125419A (en) | 2001-01-11 |
| ZA971672B (en) | 1997-08-29 |
| CN1211975A (en) | 1999-03-24 |
| NO310870B1 (en) | 2001-09-10 |
| AU717720B2 (en) | 2000-03-30 |
| IL125419A0 (en) | 1999-03-12 |
| JP2009185077A (en) | 2009-08-20 |
| DK0883610T3 (en) | 2000-09-25 |
| NO983901D0 (en) | 1998-08-25 |
| NZ331520A (en) | 2000-01-28 |
| PT883610E (en) | 2000-10-31 |
| DE19608307C1 (en) | 1997-08-28 |
| KR100453668B1 (en) | 2004-12-16 |
| ATE194602T1 (en) | 2000-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20170227 |