NO310870B1 - Fremgangsmate for fremstilling av 1,4,7,10-tetraazasyklododekan og dets derivater - Google Patents
Fremgangsmate for fremstilling av 1,4,7,10-tetraazasyklododekan og dets derivater Download PDFInfo
- Publication number
- NO310870B1 NO310870B1 NO19983901A NO983901A NO310870B1 NO 310870 B1 NO310870 B1 NO 310870B1 NO 19983901 A NO19983901 A NO 19983901A NO 983901 A NO983901 A NO 983901A NO 310870 B1 NO310870 B1 NO 310870B1
- Authority
- NO
- Norway
- Prior art keywords
- derivative
- benzylaziridine
- tetraazacyclododecane
- derivatives
- substituted
- Prior art date
Links
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 5
- CASDNPHWJOQUQX-UHFFFAOYSA-N 1-benzylaziridine Chemical compound C=1C=CC=CC=1CN1CC1 CASDNPHWJOQUQX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical compound C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000011065 in-situ storage Methods 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- -1 sulfuric acid ester Chemical class 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- JIIXMZQZEAAIJX-UHFFFAOYSA-N 1-amino-3-phenylpropan-2-ol Chemical class NCC(O)CC1=CC=CC=C1 JIIXMZQZEAAIJX-UHFFFAOYSA-N 0.000 claims 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PJXWCRXOPLGFLX-VIFPVBQESA-N (2s)-2-(benzylamino)propan-1-ol Chemical compound OC[C@H](C)NCC1=CC=CC=C1 PJXWCRXOPLGFLX-VIFPVBQESA-N 0.000 description 2
- MVAWRWBZHDXWSL-UHFFFAOYSA-N 1-benzyl-2-methylaziridine Chemical compound CC1CN1CC1=CC=CC=C1 MVAWRWBZHDXWSL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001541 aziridines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZRSDQBKGDNPFLT-UHFFFAOYSA-N ethanol;oxolane Chemical compound CCO.C1CCOC1 ZRSDQBKGDNPFLT-UHFFFAOYSA-N 0.000 description 2
- MXZROTBGJUUXID-UHFFFAOYSA-K gadobenic acid Chemical compound [H+].[H+].[Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)C(C([O-])=O)COCC1=CC=CC=C1 MXZROTBGJUUXID-UHFFFAOYSA-K 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- PGFBTQBTIYCCFJ-NSHDSACASA-N (2s)-2-(benzylamino)butan-1-ol Chemical compound CC[C@@H](CO)NCC1=CC=CC=C1 PGFBTQBTIYCCFJ-NSHDSACASA-N 0.000 description 1
- VXOJKUWHCFFUCO-UHFFFAOYSA-N 1,4,7,10-tetrabenzyl-1,4,7,10-tetrazacyclododecane Chemical compound C=1C=CC=CC=1CN(CCN(CC=1C=CC=CC=1)CCN(CC=1C=CC=CC=1)CC1)CCN1CC1=CC=CC=C1 VXOJKUWHCFFUCO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XRAGHRJPISUIDG-UHFFFAOYSA-N 1-benzyl-2-ethylaziridine Chemical compound CCC1CN1CC1=CC=CC=C1 XRAGHRJPISUIDG-UHFFFAOYSA-N 0.000 description 1
- ZPDFIIGFYAHNSK-CTHHTMFSSA-K 2-[4,10-bis(carboxylatomethyl)-7-[(2r,3s)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]acetate;gadolinium(3+) Chemical compound [Gd+3].OC[C@@H](O)[C@@H](CO)N1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 ZPDFIIGFYAHNSK-CTHHTMFSSA-K 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229960003411 gadobutrol Drugs 0.000 description 1
- 229960005451 gadoteridol Drugs 0.000 description 1
- DPNNNPAKRZOSMO-UHFFFAOYSA-K gadoteridol Chemical compound [Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 DPNNNPAKRZOSMO-UHFFFAOYSA-K 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19608307A DE19608307C1 (de) | 1996-02-26 | 1996-02-26 | Verfahren zur Herstellung von 1,4,7,10-Tetraazacyclododecan und dessen Derivaten |
| PCT/EP1997/000927 WO1997031905A1 (de) | 1996-02-26 | 1997-02-26 | Verfahren zur herstellung von 1,4,7,10-tetraazacyclododecan und dessen derivaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983901D0 NO983901D0 (no) | 1998-08-25 |
| NO983901L NO983901L (no) | 1998-08-25 |
| NO310870B1 true NO310870B1 (no) | 2001-09-10 |
Family
ID=7787168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983901A NO310870B1 (no) | 1996-02-26 | 1998-08-25 | Fremgangsmate for fremstilling av 1,4,7,10-tetraazasyklododekan og dets derivater |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0883610B1 (cs) |
| JP (2) | JP4745469B2 (cs) |
| KR (1) | KR100453668B1 (cs) |
| CN (1) | CN1081186C (cs) |
| AT (1) | ATE194602T1 (cs) |
| AU (1) | AU717720B2 (cs) |
| CA (1) | CA2247265C (cs) |
| CZ (1) | CZ290128B6 (cs) |
| DE (2) | DE19608307C1 (cs) |
| DK (1) | DK0883610T3 (cs) |
| ES (1) | ES2148837T3 (cs) |
| GR (1) | GR3034468T3 (cs) |
| HK (1) | HK1018618A1 (cs) |
| IL (1) | IL125419A (cs) |
| NO (1) | NO310870B1 (cs) |
| NZ (1) | NZ331520A (cs) |
| PL (1) | PL185927B1 (cs) |
| PT (1) | PT883610E (cs) |
| SK (1) | SK281972B6 (cs) |
| WO (1) | WO1997031905A1 (cs) |
| ZA (1) | ZA971672B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19608307C1 (de) * | 1996-02-26 | 1997-08-28 | Schering Ag | Verfahren zur Herstellung von 1,4,7,10-Tetraazacyclododecan und dessen Derivaten |
| CZ297577B6 (cs) * | 2005-10-17 | 2007-01-10 | Azacycles S. R. O. | Způsob přípravy 1,4,7,10-tetraazacyklododekanua jeho N-acylderivátů |
| DE102009057274B4 (de) | 2009-12-02 | 2011-09-01 | Bayer Schering Pharma Aktiengesellschaft | Gadobutrolherstellung mittels Trioxobicyclo-octan |
| DE102010013833A1 (de) | 2010-03-29 | 2011-09-29 | Bayer Schering Pharma Aktiengesellschaft | Herstellung von Gadobutrol mittels Dimethylformamiddimethylacetal |
| CN101845112B (zh) * | 2010-06-02 | 2011-09-14 | 华东理工大学 | 一种基于高分子纳米粒子的高灵敏性核磁共振成像造影剂的制备方法 |
| DE102010023105A1 (de) | 2010-06-04 | 2011-12-08 | Bayer Schering Pharma Aktiengesellschaft | Gadobutrolherstellung im Eintopfverfahren mittels DMF-acetal und N-Methylimidazol |
| EA201600272A1 (ru) * | 2011-04-21 | 2016-12-30 | Байер Интеллектчуал Проперти Гмбх | Получение гадобутрола высокой чистоты |
| KR102067551B1 (ko) * | 2018-04-12 | 2020-01-17 | (주) 에프엔지리서치 | 오염토양 또는 오염수질 복원용 화합물 |
| CN108794417A (zh) * | 2018-08-04 | 2018-11-13 | 许昌恒生制药有限公司 | 一种医疗诊断造影剂中间体的制备方法 |
| 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 |
| JPH11511733A (ja) * | 1995-03-10 | 1999-10-12 | ナイコムド サルター，インコーポレイテッド | Ｎ−アリールメチル−アジリジン誘導体、前記誘導体から得られる１，４，７，１０−テトラアザシクロドデカン誘導体、および、中間体としてのｎ−アリールメチル−エタノールアミンのスルホン酸エステルの製造方法 |
| DE19608307C1 (de) * | 1996-02-26 | 1997-08-28 | Schering Ag | Verfahren zur Herstellung von 1,4,7,10-Tetraazacyclododecan und dessen Derivaten |
-
1996
- 1996-02-26 DE DE19608307A patent/DE19608307C1/de not_active Expired - Fee Related
-
1997
- 1997-02-26 CZ CZ19982721A patent/CZ290128B6/cs not_active IP Right Cessation
- 1997-02-26 EP EP96946361A patent/EP0883610B1/de not_active Expired - Lifetime
- 1997-02-26 ES ES96946361T patent/ES2148837T3/es not_active Expired - Lifetime
- 1997-02-26 DE DE59702009T patent/DE59702009D1/de not_active Expired - Lifetime
- 1997-02-26 KR KR10-1998-0706649A patent/KR100453668B1/ko not_active IP Right Cessation
- 1997-02-26 CN CN97192459A patent/CN1081186C/zh not_active Expired - Lifetime
- 1997-02-26 CA CA002247265A patent/CA2247265C/en not_active Expired - Lifetime
- 1997-02-26 AU AU18772/97A patent/AU717720B2/en not_active Expired
- 1997-02-26 AT AT96946361T patent/ATE194602T1/de active
- 1997-02-26 IL IL12541997A patent/IL125419A/xx not_active IP Right Cessation
- 1997-02-26 PT PT96946361T patent/PT883610E/pt unknown
- 1997-02-26 JP JP53059297A patent/JP4745469B2/ja not_active Expired - Lifetime
- 1997-02-26 SK SK1172-98A patent/SK281972B6/sk not_active IP Right Cessation
- 1997-02-26 PL PL97328468A patent/PL185927B1/pl unknown
- 1997-02-26 NZ NZ331520A patent/NZ331520A/xx not_active IP Right Cessation
- 1997-02-26 ZA ZA9701672A patent/ZA971672B/xx unknown
- 1997-02-26 WO PCT/EP1997/000927 patent/WO1997031905A1/de active IP Right Grant
- 1997-02-26 DK DK96946361T patent/DK0883610T3/da active
-
1998
- 1998-08-25 NO NO19983901A patent/NO310870B1/no not_active IP Right Cessation
-
1999
- 1999-08-27 HK HK99103678A patent/HK1018618A1/xx not_active IP Right Cessation
-
2000
- 2000-09-21 GR GR20000402157T patent/GR3034468T3/el unknown
-
2009
- 2009-05-27 JP JP2009127490A patent/JP2009185077A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN1211975A (zh) | 1999-03-24 |
| GR3034468T3 (en) | 2000-12-29 |
| EP0883610A1 (de) | 1998-12-16 |
| HK1018618A1 (en) | 1999-12-30 |
| ZA971672B (en) | 1997-08-29 |
| SK281972B6 (sk) | 2001-09-11 |
| NZ331520A (en) | 2000-01-28 |
| DE59702009D1 (de) | 2000-08-17 |
| DK0883610T3 (da) | 2000-09-25 |
| AU1877297A (en) | 1997-09-16 |
| NO983901D0 (no) | 1998-08-25 |
| JP2009185077A (ja) | 2009-08-20 |
| ES2148837T3 (es) | 2000-10-16 |
| AU717720B2 (en) | 2000-03-30 |
| PL328468A1 (en) | 1999-02-01 |
| JP4745469B2 (ja) | 2011-08-10 |
| CA2247265C (en) | 2005-06-21 |
| CZ272198A3 (cs) | 2000-02-16 |
| KR100453668B1 (ko) | 2004-12-16 |
| SK117298A3 (en) | 1999-01-11 |
| IL125419A0 (en) | 1999-03-12 |
| NO983901L (no) | 1998-08-25 |
| CA2247265A1 (en) | 1997-09-04 |
| KR19990087248A (ko) | 1999-12-15 |
| DE19608307C1 (de) | 1997-08-28 |
| WO1997031905A1 (de) | 1997-09-04 |
| IL125419A (en) | 2001-01-11 |
| ATE194602T1 (de) | 2000-07-15 |
| CZ290128B6 (cs) | 2002-06-12 |
| JP2000505467A (ja) | 2000-05-09 |
| PL185927B1 (pl) | 2003-09-30 |
| CN1081186C (zh) | 2002-03-20 |
| EP0883610B1 (de) | 2000-07-12 |
| PT883610E (pt) | 2000-10-31 |
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