JP2001521545A - 造影剤の製造法 - Google Patents
造影剤の製造法Info
- Publication number
- JP2001521545A JP2001521545A JP54526398A JP54526398A JP2001521545A JP 2001521545 A JP2001521545 A JP 2001521545A JP 54526398 A JP54526398 A JP 54526398A JP 54526398 A JP54526398 A JP 54526398A JP 2001521545 A JP2001521545 A JP 2001521545A
- Authority
- JP
- Japan
- Prior art keywords
- lanthanide
- oxalic acid
- reaction
- oxide
- dtpa
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000002872 contrast media Substances 0.000 title description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 103
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 34
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 31
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 229910000311 lanthanide oxide Inorganic materials 0.000 claims abstract description 25
- RZESKRXOCXWCFX-UHFFFAOYSA-N 2-[bis[2-[carboxymethyl-[2-(methylamino)-2-oxoethyl]amino]ethyl]amino]acetic acid Chemical compound CNC(=O)CN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC(=O)NC RZESKRXOCXWCFX-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000008139 complexing agent Substances 0.000 claims abstract description 11
- 239000003446 ligand Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000012535 impurity Substances 0.000 claims description 12
- 238000001465 metallisation Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 6
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 4
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical group OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 4
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical group [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 239000012431 aqueous reaction media Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- IQUHNCOJRJBMSU-UHFFFAOYSA-N H3HP-DO3A Chemical compound CC(O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 IQUHNCOJRJBMSU-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 7
- -1 gadolinium Chemical class 0.000 description 6
- 238000006263 metalation reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910001938 gadolinium oxide Inorganic materials 0.000 description 4
- 229940075613 gadolinium oxide Drugs 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- HZHFFEYYPYZMNU-UHFFFAOYSA-K gadodiamide Chemical compound [Gd+3].CNC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC(=O)NC HZHFFEYYPYZMNU-UHFFFAOYSA-K 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- MQCZPHMWPRAURJ-UHFFFAOYSA-M C(C(=O)O)(=O)[O-].[O-2].[Gd+3] Chemical compound C(C(=O)O)(=O)[O-].[O-2].[Gd+3] MQCZPHMWPRAURJ-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 1
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000002059 diagnostic imaging Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910021644 lanthanide ion Inorganic materials 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Length Measuring Devices By Optical Means (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.反応促進剤としてシュウ酸またはその塩もしくは誘導体を使用することを特 徴とする、酸化ランタニドを錯化剤と水性反応媒質中で反応させることによるラ ンタニド錯体の製造方法。 2.ランタニドがガドリニウムである請求項1記載の方法。 3.反応促進剤としてシュウ酸が使用される請求項1および2のいずれか一項に 記載の方法。 4.反応促進剤として酸化ランタニド1gあたり200〜1000μgのシュウ酸を使用 する請求項1から3のいずれか一項記載の方法。 5.(a)酸化ランタニド中の不純物のレベルを決定し、そして(b)決定した不純 物のレベルが異なるバッチからの酸化ランタニドを混合しそして(あるいは)所 定の量のシュウ酸またはその塩もしくは誘導体を反応媒質に含める工程からなり 、ここで工程(b)によって金属化反応で使用される反応剤が酸化ランタニド1g あたり少なくとも50μgの全レベルでシュウ酸(または塩もしくは誘導体)ある いはシュウ酸塩を含有することを特徴とする、酸化ランタニドを錯化剤と水性媒 質中で反応させることによってランタニド錯体を製造する方法。 6.ランタニドがガドリニウムである請求項5記載の方法。 7.所定の量のシュウ酸またはそれの塩もしくは誘導体が反応媒質に含められる 請求項5および6のいずれか一項に記載の方法。 8.所定の量のシュウ酸が反応媒質に含められる請求項7記載の方法。 9.酸化ランタニドとして使用するためにシュウ酸塩不純物のレベルが酸化ラン タニド1gあたりシュウ酸少なくとも100μgである酸化ランタニドが選択される ことを特徴とする、酸化ランタニドを水性反応媒質中で錯化剤と反応させること によりランタニド錯体を製造する方法。 10.ランタニドがガドリニウムである請求項9記載の方法。 11.錯化剤がポリアミノポリカルボン酸である請求項1から10のいずれか一項に 記載の方法。 12.錯化剤がDTPA、DTPA-BMAおよびHP-DO3Aから選択される請求項11記載の方法 。 13.錯化剤がDTPA-BMAである請求項11記載の方法。 14.シュウ酸塩含有率が酸化ランタニド1gあたりシュウ酸少なくとも100μgで あるシュウ酸および(または)酸化ランタニドを配位子のランタニド金属の反応 促進剤として使用すること。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9707880.2 | 1997-04-18 | ||
GBGB9707880.2A GB9707880D0 (en) | 1997-04-18 | 1997-04-18 | Contrast agent preparation |
US4440997P | 1997-04-29 | 1997-04-29 | |
PCT/GB1998/001019 WO1998047856A1 (en) | 1997-04-18 | 1998-04-07 | Contrast agent preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2001521545A true JP2001521545A (ja) | 2001-11-06 |
JP4035625B2 JP4035625B2 (ja) | 2008-01-23 |
Family
ID=26311410
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP54526398A Expired - Lifetime JP4035625B2 (ja) | 1997-04-18 | 1998-04-07 | 造影剤の製造法 |
Country Status (19)
Country | Link |
---|---|
US (1) | US6191262B1 (ja) |
EP (1) | EP0975580B1 (ja) |
JP (1) | JP4035625B2 (ja) |
CN (1) | CN100352802C (ja) |
AT (1) | ATE224867T1 (ja) |
AU (1) | AU745970B2 (ja) |
BR (1) | BR9808924A (ja) |
CA (1) | CA2287245A1 (ja) |
CZ (1) | CZ296233B6 (ja) |
DE (1) | DE69808265T2 (ja) |
ES (1) | ES2187018T3 (ja) |
GB (1) | GB9707880D0 (ja) |
HK (1) | HK1025313A1 (ja) |
HU (1) | HUP0001861A2 (ja) |
IL (1) | IL132433A0 (ja) |
NO (1) | NO320618B1 (ja) |
NZ (1) | NZ500061A (ja) |
PL (1) | PL336208A1 (ja) |
WO (1) | WO1998047856A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013514311A (ja) * | 2009-12-16 | 2013-04-25 | ブラッコ・イメージング・ソシエタ・ペル・アチオニ | キレート化合物の製造 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2794032B1 (fr) * | 1999-05-27 | 2002-06-14 | Univ Claude Bernard Lyon | Procede pour separer en milieu aqueux des lanthanides et/ou des actinides par complexation-nanofiltration, et nouveaux complexants mis en oeuvre dans ce procede |
CN1321122C (zh) * | 2005-02-03 | 2007-06-13 | 华东师范大学 | 一种水热合成钆-二乙三胺五乙酸的方法 |
CN106008254B (zh) * | 2016-05-27 | 2018-08-21 | 南京正大天晴制药有限公司 | 一种卡地酰胺钠的精制工艺 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4647447A (en) * | 1981-07-24 | 1987-03-03 | Schering Aktiengesellschaft | Diagnostic media |
FR2669028B1 (fr) * | 1990-11-13 | 1992-12-31 | Rhone Poulenc Chimie | Procede de fabrication d'oxalates doubles de terres rares et d'ammonium et leurs utilisations pour la fabrication d'oxydes de terres rares. |
FR2674256B1 (fr) * | 1991-03-21 | 1994-07-29 | Commissariat Energie Atomique | Procede pour separer le fer et/ou le zirconium des actinides et/ou des lanthanides presents dans une solution aqueuse acide au moyen d'un propanediamide. |
-
1997
- 1997-04-18 GB GBGB9707880.2A patent/GB9707880D0/en active Pending
-
1998
- 1998-04-07 AT AT98914995T patent/ATE224867T1/de not_active IP Right Cessation
- 1998-04-07 DE DE69808265T patent/DE69808265T2/de not_active Expired - Lifetime
- 1998-04-07 HU HU0001861A patent/HUP0001861A2/hu unknown
- 1998-04-07 PL PL98336208A patent/PL336208A1/xx unknown
- 1998-04-07 IL IL13243398A patent/IL132433A0/xx unknown
- 1998-04-07 ES ES98914995T patent/ES2187018T3/es not_active Expired - Lifetime
- 1998-04-07 WO PCT/GB1998/001019 patent/WO1998047856A1/en active IP Right Grant
- 1998-04-07 EP EP98914995A patent/EP0975580B1/en not_active Expired - Lifetime
- 1998-04-07 AU AU69287/98A patent/AU745970B2/en not_active Ceased
- 1998-04-07 NZ NZ500061A patent/NZ500061A/en unknown
- 1998-04-07 BR BR9808924-2A patent/BR9808924A/pt unknown
- 1998-04-07 JP JP54526398A patent/JP4035625B2/ja not_active Expired - Lifetime
- 1998-04-07 CZ CZ0368899A patent/CZ296233B6/cs unknown
- 1998-04-07 CA CA002287245A patent/CA2287245A1/en not_active Abandoned
- 1998-04-07 CN CNB988041316A patent/CN100352802C/zh not_active Expired - Lifetime
-
1999
- 1999-10-15 US US09/419,290 patent/US6191262B1/en not_active Expired - Lifetime
- 1999-10-15 NO NO19995058A patent/NO320618B1/no not_active IP Right Cessation
-
2000
- 2000-07-25 HK HK00104602A patent/HK1025313A1/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013514311A (ja) * | 2009-12-16 | 2013-04-25 | ブラッコ・イメージング・ソシエタ・ペル・アチオニ | キレート化合物の製造 |
Also Published As
Publication number | Publication date |
---|---|
NZ500061A (en) | 2001-04-27 |
DE69808265T2 (de) | 2003-07-31 |
CZ368899A3 (cs) | 2000-04-12 |
NO320618B1 (no) | 2005-12-27 |
CN1252051A (zh) | 2000-05-03 |
NO995058D0 (no) | 1999-10-15 |
WO1998047856A1 (en) | 1998-10-29 |
GB9707880D0 (en) | 1997-06-04 |
CN100352802C (zh) | 2007-12-05 |
CZ296233B6 (cs) | 2006-02-15 |
PL336208A1 (en) | 2000-06-05 |
AU6928798A (en) | 1998-11-13 |
NO995058L (no) | 1999-10-15 |
ES2187018T3 (es) | 2003-05-16 |
EP0975580A1 (en) | 2000-02-02 |
DE69808265D1 (de) | 2002-10-31 |
AU745970B2 (en) | 2002-04-11 |
HUP0001861A2 (hu) | 2000-09-28 |
BR9808924A (pt) | 2000-08-01 |
IL132433A0 (en) | 2001-03-19 |
CA2287245A1 (en) | 1998-10-29 |
JP4035625B2 (ja) | 2008-01-23 |
ATE224867T1 (de) | 2002-10-15 |
EP0975580B1 (en) | 2002-09-25 |
US6191262B1 (en) | 2001-02-20 |
HK1025313A1 (en) | 2000-11-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2537502B2 (ja) | 1−置換−1,4,7−トリスカルボキシメチル−1,4,7,10−テトラアザシクロドデカンおよび類縁体 | |
EP0287465B1 (fr) | Ligands cycliques azotés, complexes métalliques formés par ces ligands, compositions de diagnostic contenant ces complexes et procédé de préparation des ligands | |
JP4351299B2 (ja) | 大環状キレート化剤の製造方法およびその常磁性金属イオンとのキレート化合物 | |
EP1417183B1 (en) | Multidentate aza ligands able to complex metal ions and the use thereof in diagnostics and therapy | |
JP2894839B2 (ja) | アミノホスホン酸類の非−アルカリ性精製 | |
JP2633944B2 (ja) | 錯体化合物の製造方法 | |
JP3842278B2 (ja) | 9−ニトロ−20−カンプトセシン(9−nitro−20−camptothecin)の調製および精製方法 | |
EP1602649B1 (en) | Process for the preparation of monofunctionalized 1,4,7,10-tetraazacyclododecane | |
JPH09505819A (ja) | 核磁気共鳴診断用常磁性キレート | |
CN108299322A (zh) | 一种制备高纯度钆布醇的方法 | |
JP2001521545A (ja) | 造影剤の製造法 | |
EP0773936B1 (en) | Macrocyclic chelants, their chelates and uses thereof in the diagnostic field | |
EP0815091B1 (en) | Polyazacycloalkane compounds | |
KR100544931B1 (ko) | 조영제 제조 방법 | |
EP4073045A1 (en) | Manufacturing of protected do3a | |
JP4842475B2 (ja) | 胆汁酸誘導体の製造方法 | |
EP1045838B1 (en) | 1,4,7,10-tetraazacyclododecane-1,4-diacetic acid | |
WO2009127715A1 (en) | Compounds comprising paramagnetic chelates arranged around a central core and their use in magneto resonance imaging and spectroscopy | |
JP3059488B2 (ja) | ポリアザシクロアルカン化合物 | |
CN100491333C (zh) | 高纯度烯胺类的制备方法 | |
RU2161123C1 (ru) | Способ получения окисленного графита | |
JP2003513103A (ja) | I族またはii族金属塩とのコンプレックス生成による多形相iおよびiiのフィナステライドの製造 | |
KR20060125802A (ko) | Dtpa-비스 무수물의 제조방법 | |
JP2003508537A (ja) | リン含有エチレンジアミン誘導体のカルシウム錯体 | |
JPS58216160A (ja) | キノリン誘導体の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050322 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070906 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20071002 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20071009 |
|
A72 | Notification of change in name of applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A721 Effective date: 20071009 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101109 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111109 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121109 Year of fee payment: 5 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121109 Year of fee payment: 5 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131109 Year of fee payment: 6 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |