KR960700762A - 방사활성 동위원소에 대한 xn_14s_1x' 유형의 킬레이트화제, 그의 금속 착물, 및 그의 진단 및 치료학적 용도(chelators of type xn_1s_1x' for radioactive isotopes, their metal complexes and their diagnostic and therapeutical uses) - Google Patents
방사활성 동위원소에 대한 xn_14s_1x' 유형의 킬레이트화제, 그의 금속 착물, 및 그의 진단 및 치료학적 용도(chelators of type xn_1s_1x' for radioactive isotopes, their metal complexes and their diagnostic and therapeutical uses) Download PDFInfo
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- 239000002738 chelating agent Substances 0.000 title abstract 3
- 230000001225 therapeutic effect Effects 0.000 title abstract 2
- 239000002184 metal Substances 0.000 title 1
- 230000002285 radioactive effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 239000003446 ligand Substances 0.000 claims abstract 8
- 239000012217 radiopharmaceutical Substances 0.000 claims abstract 4
- 229940121896 radiopharmaceutical Drugs 0.000 claims abstract 4
- 230000002799 radiopharmaceutical effect Effects 0.000 claims abstract 4
- 150000001787 chalcogens Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 239000000126 substance Substances 0.000 claims 5
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 3
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- -1 polyalkenyl Chemical group 0.000 claims 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 108050009340 Endothelin Proteins 0.000 claims 2
- 102000002045 Endothelin Human genes 0.000 claims 2
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052702 rhenium Inorganic materials 0.000 claims 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 229940056501 technetium 99m Drugs 0.000 claims 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 150000001299 aldehydes Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
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- 239000002308 endothelin receptor antagonist Substances 0.000 claims 1
- 150000002191 fatty alcohols Chemical class 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
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- 238000012800 visualization Methods 0.000 claims 1
- 230000001588 bifunctional effect Effects 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000001959 radiotherapy Methods 0.000 abstract 1
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Abstract
본 발명은 간헐성 칼코겐 원자를 갖는 신규한 이작용성 킬레이트화제, 이들 화합물을 함유하는 약제, 방사선 진단학 및 방사선 요법에서의 그의 용도, 및 이들 화합들을 제조하는 방법에 관한 것이다. 본 발명에 따르는 화합물은 하기 일반식(Ⅰ)의 화합물이다. M-L (Ⅰ) 상기식에서 M은 방사핵종이고, L은 일반식(Ⅱ)의 리간드이다. 놀랍게도, 간헐설 칼로겐 원자를 갖는 신규한 이작용성 킬레이트화제 및 그의 특수하게 축적되는 화합물과의 커플링 생성물이 진단 및 치료를 목적으로 하는 방사선 의약품을 제조하기에 매우 적당함을 발견하였다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (14)
- 하기 일반식(Ⅰ)의 화합물.M-L (Ⅰ)상기식에서 M은 Tc, 또는 Re의 방사핵종이고, L은 일반식 B-CO-CR1R2-A-CR3R4-CR5R6-A'-R12(Ⅱ)의 리간드이며, 여기에서, A와 A'는 동일하거나 상이하고, 는 O, S 또는 Se칼코겐 원자이며, R1, R2, R3, R4, R5및 R6는 동일하거나 상이하고, 수소 원자 및/또는 측쇄 또는 비측쇄 C1-C6알킬 전기이며, B는 잔기 -NH-(CR7R8)-(CR9R10)n-1,2-S-R11이고, 여기에서, R7및 R8는 동일하거나 상이하고, 수소 원자, 또는 비측쇄, 측쇄, 사이클릭 또는 플리사이클릭 C1-C10알킬, 알케닐, 폴리알케닐, 알키닐, 폴리알키닐, 아릴, 알킬아릴, 또는 카복시, 아미노카보닐, 알콕시카보닐, 아미노, 알데히드, 하이드록시, 옥소, 옥시 또는 탄소수 20 이하의 알콕시 그룹에 의해 임의로 치환될 수 있고 O, N, S, P, As 및 Se의 그룹 중에서 선택된 하나 또는 여러개의 헤테로원자에 의해 임의로 차단되거나 치환될 수 있는 아릴알킬 잔기이며, R9및 R10는 동일하거나, 상이하며, 수소 원자 및/또는 측쇄 또는 비측쇄 C1-C6알킬 전기이며, R11는 수소 원자, 황 보호 그룹, 또는 R7및 R8와 같은 잔기이거나, R7및 R11는 그들이 결합된 그룹과 함께 추가의 하이드록시, 옥소, 옥시 또는 탄소수 6 이하의 알콕시 그룹에 의해 이의로 치환될 수 있는 4- 내지 8-원 환을 임의로 형성하며, R12는 수소 원자 또는 칼코겐 보호 그룹이다.
- 제1항에 있어서, A 및 A'가 황 원자이고, R12가 수소 원자 또는 황 보호 그룹인 화합물.
- 제1항 또는 2항에 있어서, R7및 R8가 상이하고, R8,R9및 R10가 각각 수소 원자인 화합물
- 하기 일반식(Ⅱ)의 리간드.B-CO-CR1R2-A-CR3R4--CR5R6-A'-R12(Ⅱ)상기식에서, R1,R2,R3,R4,R5,R6,R12,A,A' 및 B는 제1항에서 정의한 바와 같다.
- 제4항에 또는 5항에 있어서, A 및 A'가 황 원자이고, R12가 수소 원자 또는 황 보호 그룹인 리간드
- 제4항 또는 5항에 있어서, R7 및 R8가 상이하고, R8, R9및 R10가 각각 수소 원자인 리간드
- 일반식(Ⅰ) 및/또는 (Ⅱ)의 화합물과 병든 조직에 선택적으로 축적되는 물질을 함유하며, 상기의 물질들 사이에는 공유결합이 존재하고, 이 결합은 물질이 펩타이드, 단백질, 항체 또는 그들의 단편과 같이 카복시 또는 아미노 그룹을 함유하는 경우에는 아미드 결합이고, 물질이 지방 알코올과 같이 하이드록시 그룹을 함유하는 경우에는 에스테르 결합이며, 물질이 알데히드 그룹을 함유하는 경우에는 이미드 결합인 콘쥬게이트.
- 제7항에 있어서, 병든 조직에 축적되는 물질이 엔도텔린, 부분 엔도텔린 서열, 엔도텔린 동족체, 엔도텔린 유도체, 또는 엔도텔린 길항제와 같은 펩타이드인 콘쥬게이트.
- 제7항에 있어서, 펩타이드가 서열,trp 또는 그의 일부분, 또는 부부 ㄴ서열, 또는 사이클릭 아미노산 서열 사이클로-(Dtrp-Dasp-pro-Dval-leu), 사이클로-(Dglu-ala-alloDile-leu-Dtrp)을 함유하는 콘쥬게이트.
- 페테크네테이트 형태의 테크네튬-99m 또는 퍼레네이트 형태의 Re를 환원제 및, 임의로 보조 리간드의 존재하에 하기 일반식(Ⅱ)의 화합물과 반응시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물을 제조하는 방법.B-CO-CR1R2-A-CR3R4--CR5R6-A'R12(Ⅱ)상기식에서, R1,R2,R3,R4,R5,R6,R12,A,A' 또는 B는 제1항에서 정의한 바와 같다.
- 하기 일반식(Ⅲ)의 화합물을 하기 반응 도식에 따라 하기 일반식(Ⅳ)의 화합물과 반응시킴을 특징으로 하여 일반식(Ⅱ)의 리간드를 제조하는 방법.X-CO-CR1R2-A-CR3R4-CR5R6-A'R12(Ⅲ)+NH2-CR7R8-(CR9R10)n=1,2-S-R11(Ⅳ)-B-CO-CR1R2-A-CR3R4-CR5R6-A'-R12(Ⅱ)상기식에서, X는 이탈 그룹이고, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12,A, A' 및 B는 제1항에서 정의한 바와 같다.
- 제4항 내지 6항 중의 한 항에 따르는 일반식(Ⅱ)의 화합물, 또는 제7항 내지 9항 중의 한 항에 따르는 콘쥬게이트, 환원제 및, 임의로 보조 리간드를 함유하며, 건조 상태 또는 용액 상태이고, 사용지침이 상기 화하물을 피테크네테이트 또는 퍼레네이트 용액 형태의 테크네튬-99m 또는 레늄과 반응시키는 지침을 포함하는 방사성 의약품을 제조하기 위한 키트.
- 제1항 내지 3항 중의 한 항에 따르는 일반식(Ⅰ)의 화합물, 또는 제7항 내지 9항 중의 한 항에 따르는 콘쥬게이트, 및 이의로 갈레누스 제제 중의 통상의 보조제를 함유하며, 화합물은 피테크네테이트 또는 퍼레네이트 용액 형태의 테크네튬-99m 또는 레늄을 사용하여 제12항에 따르는 키트 중에서 제조됨을 특징으로 하는 수용체 및/또는 죽상경화성 플라크를 함유하는 조직을 비침투적으로 생체내에 가시화하기 위한 방사성 의약품 제제.
- 제13항에 따르는 방사성 의약품 제제를 환자 체중 70kg 당 0.1mCi 내지 30mCi, 바람직하게는 0.5mCi 내지 10mCi의 양으로 적용시키고 환자에 의해 방출된 방사선을 기록하여 방사선 진단 검사를 수행하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4310999A DE4310999C2 (de) | 1993-03-31 | 1993-03-31 | Bifunktionelle chalkogenatom-unterbrochene Chelatbildner vom Typ XN¶1¶S¶1¶X' für radioaktive Isotope und deren Metallkomplexe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Mittel |
| DEP4310999.3 | 1993-03-31 | ||
| PCT/DE1994/000372 WO1994022493A1 (de) | 1993-03-31 | 1994-03-29 | Chelatbildner vom typ xn1s1x' für radioaktive isotope, deren metallkomplexe und ihre verwendung in diagnostik und therapie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR960700762A true KR960700762A (ko) | 1996-02-24 |
Family
ID=6484671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950703670A KR960700762A (ko) | 1993-03-31 | 1994-03-29 | 방사활성 동위원소에 대한 xn_14s_1x' 유형의 킬레이트화제, 그의 금속 착물, 및 그의 진단 및 치료학적 용도(chelators of type xn_1s_1x' for radioactive isotopes, their metal complexes and their diagnostic and therapeutical uses) |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5961954A (ko) |
| EP (1) | EP0692981B1 (ko) |
| JP (1) | JPH08511237A (ko) |
| KR (1) | KR960700762A (ko) |
| AT (1) | ATE179078T1 (ko) |
| AU (1) | AU692154B2 (ko) |
| CA (1) | CA2156619A1 (ko) |
| DE (2) | DE4310999C2 (ko) |
| HU (1) | HUT73489A (ko) |
| NO (1) | NO953868L (ko) |
| NZ (1) | NZ263795A (ko) |
| WO (1) | WO1994022493A1 (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4311022C2 (de) * | 1993-03-31 | 1996-07-11 | Diagnostikforschung Inst | Bifunktionelle chalkogenatom-unterbrochene Chelatbildner vom Typ S¶3¶N¶2¶ für radioaktive Isotope und deren Metallkomplexe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Mittel |
| DE19536781A1 (de) * | 1995-09-21 | 1997-03-27 | Diagnostikforschung Inst | Bifunktionelle sulfidhaltige Sulfonamid-Chelatbildner vom Typ XSNS für radioaktive Isotope |
| DE19536785A1 (de) * | 1995-09-21 | 1997-03-27 | Diagnostikforschung Inst | Bifunktionelle sulfidhaltige Sulfonamid-Chelatbildner vom Typ S¶2¶NY für radioaktive Isotope |
| DE19652374A1 (de) * | 1996-12-04 | 1998-06-10 | Schering Ag | Verwendung von Endothelin-Konjugaten in der Therapie, neue Endothelin-Konjugate, diese enthaltende Mittel, sowie Verfahren zu deren Herstellung |
| CN100528241C (zh) * | 2002-05-06 | 2009-08-19 | 恩多塞特公司 | 维生素-定向的显象剂 |
| US20080058674A1 (en) * | 2006-08-29 | 2008-03-06 | Lex Jansen | Tissue extraction device and method of using the same |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0063946A1 (en) * | 1981-04-21 | 1982-11-03 | AMERSHAM INTERNATIONAL plc | Diagnosis of kidney function |
| EP0089143A1 (en) * | 1982-03-16 | 1983-09-21 | AMERSHAM INTERNATIONAL plc | Diagnosis of kidney function |
| US4980147A (en) * | 1984-06-25 | 1990-12-25 | University Of Utah Research Foundation | Radiolabeled technetium chelates for use in renal function determinations |
| ATE66469T1 (de) * | 1985-01-14 | 1991-09-15 | Neorx Corp | Metall-radionuklid markiertes protein fuer diagnose und therapie. |
| DE3762624D1 (de) * | 1986-05-28 | 1990-06-13 | Mallinckrodt Inc | Technetiumchelate fuer die bestimmung der nierenfunktion. |
| US4861869A (en) * | 1986-05-29 | 1989-08-29 | Mallinckrodt, Inc. | Coupling agents for joining radionuclide metal ions with biologically useful proteins |
| WO1989000557A1 (en) * | 1987-07-16 | 1989-01-26 | Cockbain, Julian, Roderick, Michaelson | Aminopolycarboxylic acids and derivatives thereof |
| AU1995392A (en) * | 1991-05-08 | 1992-12-21 | Mallinckrodt Medical, Inc. | Technetium chelates to be used for determining the renal function |
| JPH0570484A (ja) * | 1991-09-12 | 1993-03-23 | Hitachi Chem Co Ltd | ペプチドおよびその塩 |
| DE69332470D1 (de) * | 1992-02-06 | 2002-12-12 | Biosynthema Inc | Liganden zur verbesserung der metallchelatbildungskinetik |
| DE4311023C2 (de) * | 1993-03-31 | 1996-05-02 | Diagnostikforschung Inst | Bifunktionelle chalkogenatom-unterbrochene Chelatbildner von Typ XN¶1¶S¶1¶O¶1¶ für radioaktive Isotope, deren Metallkomplexe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Mittel |
| DE4311021A1 (de) * | 1993-03-31 | 1994-10-27 | Diagnostikforschung Inst | Bifunktionelle Chelatbildner, deren Technetium- und Rhenium-Komplexe, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende radiopharmazeutische Mittel |
| DE4311022C2 (de) * | 1993-03-31 | 1996-07-11 | Diagnostikforschung Inst | Bifunktionelle chalkogenatom-unterbrochene Chelatbildner vom Typ S¶3¶N¶2¶ für radioaktive Isotope und deren Metallkomplexe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Mittel |
-
1993
- 1993-03-31 DE DE4310999A patent/DE4310999C2/de not_active Expired - Lifetime
-
1994
- 1994-03-29 NZ NZ263795A patent/NZ263795A/en unknown
- 1994-03-29 KR KR1019950703670A patent/KR960700762A/ko not_active Application Discontinuation
- 1994-03-29 EP EP94912442A patent/EP0692981B1/de not_active Expired - Lifetime
- 1994-03-29 AU AU65018/94A patent/AU692154B2/en not_active Ceased
- 1994-03-29 JP JP6521543A patent/JPH08511237A/ja active Pending
- 1994-03-29 US US08/530,326 patent/US5961954A/en not_active Expired - Fee Related
- 1994-03-29 HU HU9502869A patent/HUT73489A/hu unknown
- 1994-03-29 AT AT94912442T patent/ATE179078T1/de not_active IP Right Cessation
- 1994-03-29 CA CA002156619A patent/CA2156619A1/en not_active Abandoned
- 1994-03-29 DE DE59408144T patent/DE59408144D1/de not_active Expired - Lifetime
- 1994-03-29 WO PCT/DE1994/000372 patent/WO1994022493A1/de active IP Right Grant
-
1995
- 1995-09-29 NO NO953868A patent/NO953868L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU692154B2 (en) | 1998-06-04 |
| ATE179078T1 (de) | 1999-05-15 |
| HU9502869D0 (en) | 1995-11-28 |
| NZ263795A (en) | 1997-01-29 |
| DE4310999C2 (de) | 1996-07-18 |
| CA2156619A1 (en) | 1994-10-13 |
| DE59408144D1 (de) | 1999-05-27 |
| NO953868L (no) | 1995-11-23 |
| DE4310999A1 (de) | 1994-10-06 |
| JPH08511237A (ja) | 1996-11-26 |
| WO1994022493A1 (de) | 1994-10-13 |
| NO953868D0 (no) | 1995-09-29 |
| AU6501894A (en) | 1994-10-24 |
| EP0692981B1 (de) | 1999-04-21 |
| US5961954A (en) | 1999-10-05 |
| HUT73489A (en) | 1996-08-28 |
| EP0692981A1 (de) | 1996-01-24 |
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