JPWO2018051197A5 - - Google Patents
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- JPWO2018051197A5 JPWO2018051197A5 JP2019515409A JP2019515409A JPWO2018051197A5 JP WO2018051197 A5 JPWO2018051197 A5 JP WO2018051197A5 JP 2019515409 A JP2019515409 A JP 2019515409A JP 2019515409 A JP2019515409 A JP 2019515409A JP WO2018051197 A5 JPWO2018051197 A5 JP WO2018051197A5
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- -1 cyclen metal complex Chemical class 0.000 claims description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 229910052685 Curium Inorganic materials 0.000 claims description 6
- 229910052771 Terbium Inorganic materials 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052695 Americium Inorganic materials 0.000 claims description 5
- 229910052694 Berkelium Inorganic materials 0.000 claims description 5
- 229910052684 Cerium Inorganic materials 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 5
- 229910052691 Erbium Inorganic materials 0.000 claims description 5
- 229910052693 Europium Inorganic materials 0.000 claims description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052765 Lutetium Inorganic materials 0.000 claims description 5
- 229910052773 Promethium Inorganic materials 0.000 claims description 5
- 229910052772 Samarium Inorganic materials 0.000 claims description 5
- 229910052770 Uranium Inorganic materials 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- LXQXZNRPTYVCNG-UHFFFAOYSA-N americium atom Chemical compound [Am] LXQXZNRPTYVCNG-UHFFFAOYSA-N 0.000 claims description 5
- PWVKJRSRVJTHTR-UHFFFAOYSA-N berkelium atom Chemical compound [Bk] PWVKJRSRVJTHTR-UHFFFAOYSA-N 0.000 claims description 5
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 5
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 5
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 claims description 5
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 claims description 5
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 5
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims description 5
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 4
- 229910052776 Thorium Inorganic materials 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 claims 4
- 238000003384 imaging method Methods 0.000 claims 4
- 210000003734 kidney Anatomy 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- XBXHBDPVWILCAG-UAFMIMERSA-N 2-[(2R,5R,8R,11R)-4,7,10-tris(carboxymethyl)-2,5,8,11-tetraethyl-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound CC[C@@H]1CN([C@@H](CN([C@@H](CN([C@@H](CN1CC(=O)O)CC)CC(=O)O)CC)CC(=O)O)CC)CC(=O)O XBXHBDPVWILCAG-UAFMIMERSA-N 0.000 claims 1
- XBXHBDPVWILCAG-MUGJNUQGSA-N 2-[(2S,5S,8S,11S)-4,7,10-tris(carboxymethyl)-2,5,8,11-tetraethyl-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound CC[C@H]1CN([C@H](CN([C@H](CN([C@H](CN1CC(=O)O)CC)CC(=O)O)CC)CC(=O)O)CC)CC(=O)O XBXHBDPVWILCAG-MUGJNUQGSA-N 0.000 claims 1
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 claims 1
- 229910052688 Gadolinium Inorganic materials 0.000 claims 1
- 238000002591 computed tomography Methods 0.000 claims 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims 1
- 238000002595 magnetic resonance imaging Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002600 positron emission tomography Methods 0.000 claims 1
- 229910052775 Thulium Inorganic materials 0.000 description 6
- 229910052768 actinide Inorganic materials 0.000 description 6
- 150000001255 actinides Chemical class 0.000 description 6
- 229910052779 Neodymium Inorganic materials 0.000 description 4
- 229910052777 Praseodymium Inorganic materials 0.000 description 4
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 4
- 229910052689 Holmium Inorganic materials 0.000 description 3
- 229910052769 Ytterbium Inorganic materials 0.000 description 3
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- 229910052746 lanthanum Inorganic materials 0.000 description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 3
- 229910052727 yttrium Inorganic materials 0.000 description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 3
- HHLZCENAOIROSL-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound OC(=O)CN1CCNCCN(CC(O)=O)CCN(CC(O)=O)CC1 HHLZCENAOIROSL-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000000034 method Methods 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 1
Description
一実施形態において、ＤＯＴＡ、ＤＯ３Ａ、ＤＯ２Ａ、ＤＯ１Ａ、およびサイクレンのベースリガンドを含む、本発明のキラルなサイクレンリガンドは、ｐブロック元素、ｄブロック元素、およびｆブロック元素からなる群から選択される金属と錯体を形成できる。好ましい実施形態において、ｐブロック元素は、アルミニウム、ガリウム、およびインジウムからなる群から選択される。好ましい実施形態において、ｄブロック元素は、鉄、ニッケル、マンガン、コバルト、クロム、イットリウム、ジルコニウム、亜鉛、および銅からなる群から選択できる。別の好ましい実施形態において、ｆブロック元素は、ランタニドからなる群から選択できる。ランタニドは、ランタン、セリウム、プラセオジム、ネオジム、プロメチウム、サマリウム、ユウロピウム、ガドリニウム、テルビウム、ジスプロシウム、ホルミウム、エルビウム、ツリウム、イッテルビウム、およびルテチウムからなる群から選択できる。別の好ましい実施形態において、ｆブロック元素は、アクチニドからなる群から選択できる。アクチニドは、トリウム、ウラン、アメリシウム、キュリウム、およびバークリウムからなる群から選択できる。
In one embodiment, the chiral cyclone ligands of the invention, including DOTA, DO3A, DO2A, DO1A, and a base ligand for cyclone, are selected from the group consisting of p-block elements, d-block elements, and f-block elements. Can form a complex with a metal. In a preferred embodiment, the p-block element is selected from the group consisting of aluminum, gallium, and indium. In a preferred embodiment, the d-block element can be selected from the group consisting of iron, nickel, manganese , cobalt, chromium, yttrium, zirconium, zinc, and copper. In another preferred embodiment, the f-block element can be selected from the group consisting of lanthanides. Lantanide can be selected from the group consisting of lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadrinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. In another preferred embodiment, the f-block element can be selected from the group consisting of actinides. Actinide can be selected from the group consisting of thorium, uranium, americium, curium, and berkelium.
ステップ（ｇ）において、キラルなサイクレン金属錯体は、当技術分野で公知の古典的な手順にしたがって合成できる。金属は、ｐブロック元素、ｄブロック元素、およびｆブロック元素からなる群から選択できる。好ましい実施形態において、ｐブロック元素は、アルミニウム、ガリウム、およびインジウムからなる群から選択される。好ましい実施形態において、ｄブロック元素は、鉄、ニッケル、マンガン、コバルト、クロム、イットリウム、ジルコニウム、亜鉛、および銅からなる群から選択できる。別の好ましい実施形態において、ｆブロック元素は、ランタニドからなる群から選択できる。ランタニドは、ランタン、セリウム、プラセオジム、ネオジム、プロメチウム、サマリウム、ユウロピウム、ガドリニウム、テルビウム、ジスプロシウム、ホルミウム、エルビウム、ツリウム、イッテルビウム、およびルテチウムからなる群から選択できる。別の好ましい実施形態において、ｆブロック元素は、アクチニドからなる群から選択できる。アクチニドは、トリウム、ウラン、アメリシウム、キュリウム、およびバークリウムからなる群から選択できる。
In step (g), the chiral cyclen metal complex can be synthesized according to classical procedures known in the art. The metal can be selected from the group consisting of p-block elements, d-block elements, and f-block elements. In a preferred embodiment, the p-block element is selected from the group consisting of aluminum, gallium, and indium. In a preferred embodiment, the d-block element can be selected from the group consisting of iron, nickel, manganese , cobalt, chromium, yttrium, zirconium, zinc, and copper. In another preferred embodiment, the f-block element can be selected from the group consisting of lanthanides. Lantanide can be selected from the group consisting of lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadrinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. In another preferred embodiment, the f-block element can be selected from the group consisting of actinides. Actinide can be selected from the group consisting of thorium, uranium, americium, curium, and berkelium.
ステップ（ｄ）において、キラルなＤＯ３Ａベース金属錯体は、当技術分野で公知の古典的な手順にしたがって合成できる。金属は、ｐブロック元素、ｄブロック元素、およびｆブロック元素からなる群から選択される金属からなる群から選択できる。好ましい実施形態において、ｐブロック元素は、アルミニウム、ガリウム、およびインジウムからなる群から選択される。好ましい実施形態において、ｄブロック元素は、鉄、ニッケル、マンガン、コバルト、クロム、イットリウム、ジルコニウム、亜鉛、および銅からなる群から選択できる。別の好ましい実施形態において、ｆブロック元素は、ランタニドからなる群から選択できる。ランタニドは、ランタン、セリウム、プラセオジム、ネオジム、プロメチウム、サマリウム、ユウロピウム、ガドリニウム、テルビウム、ジスプロシウム、ホルミウム、エルビウム、ツリウム、イッテルビウム、およびルテチウムからなる群から選択できる。別の好ましい実施形態において、ｆブロック元素は、アクチニドからなる群から選択できる。アクチニドは、トリウム、ウラン、アメリシウム、キュリウム、およびバークリウムからなる群から選択できる。
In step (d), the chiral DO3A-based metal complex can be synthesized according to classical procedures known in the art. The metal can be selected from the group consisting of metals selected from the group consisting of p-block elements, d-block elements, and f-block elements. In a preferred embodiment, the p-block element is selected from the group consisting of aluminum, gallium, and indium. In a preferred embodiment, the d-block element can be selected from the group consisting of iron, nickel, manganese , cobalt, chromium, yttrium, zirconium, zinc, and copper. In another preferred embodiment, the f-block element can be selected from the group consisting of lanthanides. Lantanide can be selected from the group consisting of lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadrinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. In another preferred embodiment, the f-block element can be selected from the group consisting of actinides. Actinide can be selected from the group consisting of thorium, uranium, americium, curium, and berkelium.
別の実施形態において、１つまたは複数の金属は、アルミニウム、ガリウム、インジウム、鉄、ニッケル、マンガン、コバルト、クロム、イットリウム、ジルコニウム、亜鉛、銅、ランタン、セリウム、プラセオジム、ネオジム、プロメチウム、サマリウム、ユウロピウム、ガドリニウム、テルビウム、ジスプロシウム、ホルミウム、エルビウム、ツリウム、イッテルビウム、ルテチウム、トリウム、ウラン、アメリシウム、キュリウム、およびバークリウムからなる群から選択される。
In another embodiment, the metal may be aluminum, gallium, indium, iron, nickel, manganese , cobalt, chromium, thulium, zinc, zinc, copper, lantern, cerium, praseodymium, neodymium, promethium, samarium, It is selected from the group consisting of europium, gadrinium, terbium, dysprosium, formium, erbium, thulium, itterbium, lutetium, thulium, uranium, americium, curium, and berkelium.
Claims (9)
（式中、Ｒ 1 、Ｒ 2 、Ｒ 3 、およびＲ 4 の各々が－（ＣＨ 2 ） 4 ＮＨ 2 であるか、または、Ｒ 1 、Ｒ 2 、Ｒ 3 、およびＲ 4 の各々がエチルであり、Ｘ1、Ｘ2、Ｘ3、およびＸ4の各々が－ＣＨ2ＣＯ2Ｈである）のサイクレン、および１つまたは複数の金属を含み、
金属錯体が前記サイクレンおよび前記１つまたは複数の金属の間で形成される、サイクレン金属錯体。 A cyclen metal complex for use in liver or kidney imaging, according to formula (I) :.
(In the equation, each of R 1 , R 2 , R 3 , and R 4 is − (CH 2 ) 4 NH 2 , or each of R 1 , R 2 , R 3 , and R 4 is ethyl. Yes, each of X 1 , X 2 , X 3 , and X 4 contains -CH 2 CO 2 H) cyclen, and one or more metals.
A cyclen metal complex in which a metal complex is formed between the cyclen and the one or more metals.
２，２’，２’’，２’’’－（（２Ｓ，５Ｓ，８Ｓ，１１Ｓ）－２，５，８，１１－テトラエチル－１，４，７，１０－テトラアザシクロドデカン－１，４，７，１０－テトライル）四酢酸；
２，２’，２’’，２’’’－（（２Ｒ，５Ｒ，８Ｒ，１１Ｒ）－２，５，８，１１－テトラエチル－１，４，７，１０－テトラアザシクロドデカン－１，４，７，１０－テトライル）四酢酸；および
２，２’，２’’，２’’’－（（２Ｓ，５Ｓ，８Ｓ，１１Ｓ）－２，５，８，１１－テトラキス（４－アミノブチル）－１，４，７，１０－テトラアザシクロドデカン－１，４，７，１０－テトライル）四酢酸
からなる群から選択される、請求項１から３までのいずれか１項に記載の使用のためのサイクレン金属錯体。 The cyclen of formula (I)
2,2', 2 '', 2'''-((2S, 5S, 8S, 11S) -2,5,8,11-tetraethyl-1,4,7,10-tetraazacyclododecane-1, 4,7,10-tetrayl) tetraacetic acid;
2,2', 2'', 2'''-((2R, 5R, 8R, 11R) -2,5,8,11-tetraethyl-1,4,7,10-tetraazacyclododecane-1, 4,7,10-tetrayl) tetraacetic acid; and
2,2', 2'', 2'''-((2S, 5S, 8S, 11S) -2,5,8,11-tetrakis (4-aminobutyl) -1,4,7,10-tetra Azacyclododecane-1,4,7,10-tetrayl) tetraacetic acid
The cyclen metal complex for use according to any one of claims 1 to 3, selected from the group consisting of.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662396785P | 2016-09-19 | 2016-09-19 | |
| US62/396,785 | 2016-09-19 | ||
| PCT/IB2017/053771 WO2018051197A1 (en) | 2016-09-19 | 2017-06-23 | Chiral cyclen compounds and their uses |
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| JP2019529439A JP2019529439A (en) | 2019-10-17 |
| JP2019529439A5 JP2019529439A5 (en) | 2020-08-06 |
| JPWO2018051197A5 true JPWO2018051197A5 (en) | 2022-06-01 |
| JP7421790B2 JP7421790B2 (en) | 2024-01-25 |
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| US (1) | US11357873B2 (en) |
| EP (1) | EP3515896A4 (en) |
| JP (1) | JP7421790B2 (en) |
| CN (1) | CN109963839A (en) |
| WO (1) | WO2018051197A1 (en) |
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| 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 |
| FR3092580B1 (en) * | 2019-02-08 | 2021-03-19 | Centre Nat Rech Scient | New azobenzene derivatives, their preparation process and their use for the therapeutic treatment associated with ionizing radiations |
| CN110286168B (en) * | 2019-07-03 | 2023-03-03 | 浙江普利药业有限公司 | Method for determining polyamino polycarboxyl compound in developer |
| CN111875667B (en) * | 2020-07-16 | 2021-12-21 | 南方科技大学 | Organic metal chelate, preparation method and application thereof, and probe |
| CN114105983B (en) * | 2021-11-09 | 2023-08-11 | 国科温州研究院(温州生物材料与工程研究所) | Preparation and application of chiral 1,4,7, 10-tetraaza-2, 6-pyridine cycloparaffin derivative and metal chelate thereof |
| CN114560821A (en) * | 2022-03-16 | 2022-05-31 | 国科温州研究院(温州生物材料与工程研究所) | Cyclic Gd (III) complex and preparation method and application thereof |
| JP2024513275A (en) * | 2022-03-16 | 2024-03-25 | 国科温州研究院(温州生物材料与工程研究所) | Cyclic Gd(III) complex and its preparation and use |
| EP4335840A1 (en) * | 2022-09-09 | 2024-03-13 | Bayer Aktiengesellschaft | New contrast agents for use in diagnostic imaging |
| CN116891417A (en) * | 2023-09-11 | 2023-10-17 | 成都傲科新技术有限责任公司 | Synthesis method of N, N-bis (carboxymethyl) -L-lysine |
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| US6693190B1 (en) * | 1994-05-11 | 2004-02-17 | Bracco International B.V. | Enhanced relaxivity monomeric and multimeric compounds |
| IT1291624B1 (en) * | 1997-04-18 | 1999-01-11 | Bracco Spa | COMPLEX CHELATES OF PARAMAGNETIC METALS WITH LOW TOXICITY |
| EP1466629A1 (en) * | 2003-04-11 | 2004-10-13 | BRACCO IMAGING S.p.A. | Adducts between magnetic resonance shift reagents and substrates containing exchangeable protons for "CEST" applications |
| CN1795015A (en) * | 2003-05-23 | 2006-06-28 | 埃匹克斯医药品股份有限公司 | Optically pure and enriched isomers of chelating ligands and contrast agents |
| US20060239913A1 (en) | 2003-06-25 | 2006-10-26 | Marc Port | Peptide conjugate for magnetic resonance imaging |
| US20060210479A1 (en) * | 2004-08-10 | 2006-09-21 | Dow Global Technologies Inc. | Targeting chelants and chelates |
| EP2065057A3 (en) * | 2006-03-15 | 2009-08-12 | Mallinckrodt Inc. | Chelating conjugates having a substituted aromatic moiety and derivatives thereof |
| CN100551910C (en) * | 2007-01-11 | 2009-10-21 | 清华大学 | Have compound of styryl and application thereof that nitrogen heterocyclic ring is modified |
| CN102827149B (en) * | 2012-09-06 | 2014-10-01 | 中国工程物理研究院核物理与化学研究所 | Fullerene monomacrocyclic polyamine derivative and preparation method thereof |
| CN103242255B (en) * | 2013-04-28 | 2015-01-14 | 厦门大学 | Evans blue complex as well as preparation method and application thereof |
| CN104447598B (en) * | 2013-09-18 | 2017-09-22 | 浙江大德药业集团有限公司 | CA 4 cyclen derivatives and its antitumor properties |
| GB201417067D0 (en) * | 2014-09-26 | 2014-11-12 | South African Nuclear Energy | Radiopharmaceutical conjugate |
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