WO1994022368B1 - Perfluoro-1h-1h-neopentyl containing contrast agents and method to use same - Google Patents
Perfluoro-1h-1h-neopentyl containing contrast agents and method to use sameInfo
- Publication number
- WO1994022368B1 WO1994022368B1 PCT/US1994/002477 US9402477W WO9422368B1 WO 1994022368 B1 WO1994022368 B1 WO 1994022368B1 US 9402477 W US9402477 W US 9402477W WO 9422368 B1 WO9422368 B1 WO 9422368B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- perfluoro
- group
- neopentyl
- aliphatic hydrocarbon
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 3
- 239000002872 contrast media Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 238000002595 magnetic resonance imaging Methods 0.000 claims 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000002616 MRI contrast agent Substances 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 239000000412 dendrimer Substances 0.000 claims 1
- 229920000736 dendritic polymer Polymers 0.000 claims 1
- 229940031098 ethanolamine Drugs 0.000 claims 1
- 125000001924 fatty-acyl group Chemical group 0.000 claims 1
- 229960005150 glycerol Drugs 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims 1
- 229960000367 inositol Drugs 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 230000005298 paramagnetic effect Effects 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 claims 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims 1
- 229960001153 serine Drugs 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- UPWGQKDVAURUGE-KTKRTIGZSA-N 2-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(CO)CO UPWGQKDVAURUGE-KTKRTIGZSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000002059 diagnostic imaging Methods 0.000 abstract 1
- 239000002960 lipid emulsion Substances 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000003325 tomography Methods 0.000 abstract 1
Abstract
Organic compounds for diagnostic imaging which contain at least one aryl group which has been derivatized to contain at least one perfluoro-1H,1H-neopentyl moiety are provided. The perfluoro-1H, 1H-neopentyl groups produce a single magnetic resonance to insure a maximum signal to noise ratio. One compound disclosed is 2-O-oleoylglycerol 1,3-bis(7'-{3',5'-di[2'',2''-di(trifluoromethyl)3'',3'',3''-trifluoropropyl]phenyl}heptanoate). In the preferred embodiment, a lipid emulsion is provided as a carrier vehicle to deliver the derivitized analog to a mammalian recipient. Methods to use these compounds in MRI and computerized tomography are provided.
Claims
1. A biological or pharmaceutical compound derivatized to contain at least one group having the formula :
2. The compound of claim 1 wherein said compound is a dendrimer.
3. The compound of claim 1 wherein said compound is a paramagnetic chelator.
4. The compound of claim 1, wherein said compound contains iodine.
5. A compound of the general formula:
wherein R is a fatty acyl group with 3-20 carbon atoms, n is 0-18 and m is 0-18.
6. The compound of claim 5 wherein R includes a saturated fatty acid.
7. The compound of claim 5 wherein R includes an unsaturated fatty acid.
8. The compound of claim 5 wherein n = 6 and = 6.
9. A composition suitable for use as an MRI contrast agent comprising the compound of claims 1-3, 5-8 or 11 and a suitable carrier.
10. A method of magnetic resonance imaging comprising the steps of :
(a) administering an effective amount of the composition of claim 9 to a mammal; and
(b) when said composition has reached the site to be imaged, performing magnetic resonance imaging of said site.
11. A compound of the general formula:
O
II
CH2- O — c- A" R 1 o
CH — O — C — AX 2— R π2
CH2 O Q
33
wherein Q is
0 -0
II c- A^ R^ or — P—OR
0
wherein A1, A2 and A3 are each selected from the group consisting of
saturated and unsaturated aliphatic hydrocarbon chains,
amine substituted saturated and unsaturated aliphatic hydrocarbon chains, and
amide substituted saturated and unsaturated aliphatic hydrocarbon chains, and
34
wherein R1, R2 and R3 have the formula:
wherein R4, if present, is selected from the group consisting of
Hydrogen, Choline, Ethanolamine, Serine, Glycerol, or myo-Inositol.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT94912759T ATE192778T1 (en) | 1993-03-26 | 1994-03-09 | PERFLUORO-1H-1H-NEOPENTYL CONTRAST AGENT AND METHOD OF USE THEREOF |
| JP6522078A JPH08508729A (en) | 1993-03-26 | 1994-03-09 | Contrast agent containing perfluoro-1H-1H-neopentyl and method of using the same |
| DE69424424T DE69424424T2 (en) | 1993-03-26 | 1994-03-09 | PERFLUORO-1H-1H-NEOPENTYL CONTRASTING AGENT AND METHOD FOR ITS USE |
| EP94912759A EP0707624B1 (en) | 1993-03-26 | 1994-03-09 | Perfluoro-1h-1h-neopentyl containing contrast agents and method to use same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/037,279 | 1993-03-26 | ||
| US08/037,279 US5401493A (en) | 1993-03-26 | 1993-03-26 | Perfluoro-1H,-1H-neopentyl containing contrast agents and method to use same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1994022368A1 WO1994022368A1 (en) | 1994-10-13 |
| WO1994022368B1 true WO1994022368B1 (en) | 1994-11-10 |
Family
ID=21893476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/002477 WO1994022368A1 (en) | 1993-03-26 | 1994-03-09 | Perfluoro-1h-1h-neopentyl containing contrast agents and method to use same |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5401493A (en) |
| EP (1) | EP0707624B1 (en) |
| JP (1) | JPH08508729A (en) |
| AT (1) | ATE192778T1 (en) |
| CA (1) | CA2158279A1 (en) |
| DE (1) | DE69424424T2 (en) |
| ES (1) | ES2146256T3 (en) |
| WO (1) | WO1994022368A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9205298A (en) * | 1991-09-17 | 1993-05-01 | Steven Carl Quay | GASEOUS ULTRASOUND CONTRASTING MEDIA AND METHOD FOR SELECTING GASES TO BE USED AS ULTRASOUND CONTRASTING MEDIA |
| US5558855A (en) * | 1993-01-25 | 1996-09-24 | Sonus Pharmaceuticals | Phase shift colloids as ultrasound contrast agents |
| IL108416A (en) | 1993-01-25 | 1998-10-30 | Sonus Pharma Inc | Phase shift colloids as ultrasound contrast agents |
| CZ191695A3 (en) * | 1993-01-25 | 1996-05-15 | Sonus Pharma Inc | Biologically compatible contrast agent, process of its preparation and representation method by ultrasound |
| US5695740A (en) * | 1993-05-12 | 1997-12-09 | The Board Of Regents Of The University Of Nebraska | Perfluorocarbon ultrasound contrast agent comprising microbubbles containing a filmogenic protein and a saccharide |
| US5701899A (en) * | 1993-05-12 | 1997-12-30 | The Board Of Regents Of The University Of Nebraska | Perfluorobutane ultrasound contrast agent and methods for its manufacture and use |
| JPH0797340A (en) * | 1993-06-03 | 1995-04-11 | Terumo Corp | Mri contrast medium composition |
| WO1998053855A1 (en) * | 1997-05-30 | 1998-12-03 | Alliance Pharmaceutical Corp. | Methods and apparatus for monitoring and quantifying the movement of fluid |
| US5622687A (en) * | 1994-11-15 | 1997-04-22 | Molecular Biosystems, Inc. | Calixarene conjugates useful as MRI and CT diagnostic imaging agents |
| US5660815A (en) * | 1995-04-28 | 1997-08-26 | Molecular Biosystems, Inc. | Water soluble fluorinated fatty acid sulfonate derivatives useful as magnetic resonance imaging agents |
| US5654452A (en) * | 1995-06-07 | 1997-08-05 | Molecular Biosystems, Inc. | Lipophilic contrast agents for use in hepatocyte-selective oil-in-water emulsions |
| US5648098A (en) * | 1995-10-17 | 1997-07-15 | The Board Of Regents Of The University Of Nebraska | Thrombolytic agents and methods of treatment for thrombosis |
| DE19603033A1 (en) | 1996-01-19 | 1997-07-24 | Schering Ag | Perfluoroalkyl-containing metal complexes, processes for their preparation and their use in NMR diagnostics |
| US6180113B1 (en) | 1996-02-23 | 2001-01-30 | Schering Ag | Pharmaceutical agents that contain perfluoroalkyl-containing metal complexes |
| DE19608278A1 (en) * | 1996-02-23 | 1997-08-28 | Schering Ag | Pharmaceutical compositions containing perfluoroalkyl-containing metal complexes, and their use in tumor therapy and interventional radiology |
| US6245747B1 (en) | 1996-03-12 | 2001-06-12 | The Board Of Regents Of The University Of Nebraska | Targeted site specific antisense oligodeoxynucleotide delivery method |
| US5849727A (en) * | 1996-06-28 | 1998-12-15 | Board Of Regents Of The University Of Nebraska | Compositions and methods for altering the biodistribution of biological agents |
| NL1004362C2 (en) * | 1996-10-25 | 1998-04-28 | Stichting Vakraad Voor De Meub | Device for movably positioning a workpiece for machining. |
| DE19731300C1 (en) * | 1997-07-11 | 1999-01-21 | Schering Ag | Triiodoaromatics containing perfluoroalkyl groups, process for their preparation and their use as contrast agents |
| BR0013171A (en) | 1999-07-29 | 2002-05-28 | Epix Medical Inc | Multimedia agents for objectification imaging via multi-site connection |
| US20030113267A1 (en) * | 1999-12-29 | 2003-06-19 | Knopp Michael V. | Colon contrast enhanced imaging |
| TWI221406B (en) * | 2001-07-30 | 2004-10-01 | Epix Medical Inc | Systems and methods for targeted magnetic resonance imaging of the vascular system |
| US20040126400A1 (en) * | 2002-05-03 | 2004-07-01 | Iversen Patrick L. | Delivery of therapeutic compounds via microparticles or microbubbles |
| AR047692A1 (en) * | 2003-07-10 | 2006-02-08 | Epix Medical Inc | IMAGES OF STATIONARY WHITE |
| WO2006059252A2 (en) * | 2004-11-12 | 2006-06-08 | Neurochem (International) Limited | Methods and fluorinated compositions for treating amyloid-related diseases |
| WO2006096499A2 (en) * | 2005-03-04 | 2006-09-14 | Washington University | Mr coronary angiography with a fluorinated nanoparticle contrast agent at 1.5 t |
| US7538236B2 (en) * | 2006-01-04 | 2009-05-26 | Suresh Narine | Bioplastics, monomers thereof, and processes for the preparation thereof from agricultural feedstocks |
| DE102006049821A1 (en) | 2006-10-18 | 2008-04-24 | Bayer Schering Pharma Aktiengesellschaft | New, well tolerated metal chelates, for use as radiodiagnostic, radiotherapeutic or NMR and X-ray diagnostic agents, contain chelator and perfluorinated polyethylene glycol residues |
| JP2012526129A (en) * | 2009-05-04 | 2012-10-25 | ワシントン・ユニバーシティ | PET radiotracer for imaging fatty acid metabolism and storage |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4187252A (en) * | 1977-08-26 | 1980-02-05 | Suntech, Inc. | Tetramethylpentane blood substitutes |
| US4110474A (en) * | 1977-08-26 | 1978-08-29 | Suntech, Inc. | Tetramethylpentane blood substitutes |
| US4957939A (en) * | 1981-07-24 | 1990-09-18 | Schering Aktiengesellschaft | Sterile pharmaceutical compositions of gadolinium chelates useful enhancing NMR imaging |
| US4647447A (en) * | 1981-07-24 | 1987-03-03 | Schering Aktiengesellschaft | Diagnostic media |
| US4943595A (en) * | 1981-09-08 | 1990-07-24 | The Green Cross Corporation | Perfluorochemicals and process for preparing the same |
| US4775522A (en) * | 1983-03-04 | 1988-10-04 | Children's Hospital Research Foundation, A Division Of Children's Hospital Medical Center | NMR compositions for indirectly detecting a dissolved gas in an animal |
| US4558279A (en) * | 1983-03-07 | 1985-12-10 | University Of Cincinnati | Methods for detecting and imaging a temperature of an object by nuclear magnetic resonance |
| GB8413772D0 (en) * | 1984-05-30 | 1984-07-04 | Nyegaard & Co As | Chemical compounds |
| US4535184A (en) * | 1984-06-08 | 1985-08-13 | E. I. Du Pont De Nemours And Company | Tris(disubstituted amino)sulfonium perfluorocarbanion salts |
| US4612185A (en) * | 1984-10-15 | 1986-09-16 | Mallinckrodt, Inc. | Methods and compositions for enhancing magnetic resonance imaging |
| GB8801646D0 (en) * | 1988-01-26 | 1988-02-24 | Nycomed As | Chemical compounds |
| NL8801937A (en) * | 1988-08-03 | 1990-03-01 | Optische Ind De Oude Delft Nv | DOSEMETER FOR IONIZING RADIATION. |
| US5116599A (en) * | 1989-07-31 | 1992-05-26 | Johns Hopkins Univ. | Perfluoro-t-butyl-containing compounds for use in fluorine-19 nmr and/or mri |
-
1993
- 1993-03-26 US US08/037,279 patent/US5401493A/en not_active Expired - Fee Related
-
1994
- 1994-03-09 EP EP94912759A patent/EP0707624B1/en not_active Expired - Lifetime
- 1994-03-09 WO PCT/US1994/002477 patent/WO1994022368A1/en active IP Right Grant
- 1994-03-09 ES ES94912759T patent/ES2146256T3/en not_active Expired - Lifetime
- 1994-03-09 DE DE69424424T patent/DE69424424T2/en not_active Expired - Fee Related
- 1994-03-09 JP JP6522078A patent/JPH08508729A/en active Pending
- 1994-03-09 CA CA002158279A patent/CA2158279A1/en not_active Abandoned
- 1994-03-09 AT AT94912759T patent/ATE192778T1/en not_active IP Right Cessation
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