ZA200507437B - Trimeric macrocyclically substituted benzene derivatives - Google Patents
Trimeric macrocyclically substituted benzene derivatives Download PDFInfo
- Publication number
- ZA200507437B ZA200507437B ZA200507437A ZA200507437A ZA200507437B ZA 200507437 B ZA200507437 B ZA 200507437B ZA 200507437 A ZA200507437 A ZA 200507437A ZA 200507437 A ZA200507437 A ZA 200507437A ZA 200507437 B ZA200507437 B ZA 200507437B
- Authority
- ZA
- South Africa
- Prior art keywords
- nhcoch
- stands
- chz
- hal
- metal
- Prior art date
Links
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 238000003745 diagnosis Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 150000004696 coordination complex Chemical class 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000010253 intravenous injection Methods 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 238000012800 visualization Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000001768 cations Chemical group 0.000 claims description 2
- 230000002950 deficient Effects 0.000 claims description 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical compound C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 claims description 2
- RRBYUSWBLVXTQN-VZCHMASFSA-N tricyclene Natural products C([C@@H]12)C3C[C@H]1C2(C)C3(C)C RRBYUSWBLVXTQN-VZCHMASFSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 9
- 239000008177 pharmaceutical agent Substances 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 210000004185 liver Anatomy 0.000 claims 4
- 210000001015 abdomen Anatomy 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 210000004204 blood vessel Anatomy 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 238000001361 intraarterial administration Methods 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 208000018389 neoplasm of cerebral hemisphere Diseases 0.000 claims 2
- 239000012266 salt solution Substances 0.000 claims 2
- 229910052693 Europium Inorganic materials 0.000 claims 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 claims 1
- IOIFRTZBJMZZFO-UHFFFAOYSA-N dysprosium(3+) Chemical compound [Dy+3] IOIFRTZBJMZZFO-UHFFFAOYSA-N 0.000 claims 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000002872 contrast media Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 10
- 229940039231 contrast media Drugs 0.000 description 9
- -1 pent-4-enecarbonyl Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000003384 imaging method Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002697 interventional radiology Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003690 nonionic contrast media Substances 0.000 description 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical class BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- IZOOGPBRAOKZFK-UHFFFAOYSA-K gadopentetate Chemical compound [Gd+3].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O IZOOGPBRAOKZFK-UHFFFAOYSA-K 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000012011 nucleophilic catalyst Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000008673 vomiting Effects 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0438—Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/085—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier conjugated systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Radiology & Medical Imaging (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10307759A DE10307759B3 (de) | 2003-02-19 | 2003-02-19 | Trimere makrocyclisch substituierte Benzolderivate, deren Herstellung und Verwendung als Kontrastmittel sowie diese enthaltende pharmazeutische Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200507437B true ZA200507437B (en) | 2007-02-28 |
Family
ID=32891780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200507437A ZA200507437B (en) | 2003-02-19 | 2005-09-15 | Trimeric macrocyclically substituted benzene derivatives |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1594851A1 (pt) |
| JP (1) | JP2006514664A (pt) |
| KR (1) | KR20050105474A (pt) |
| CN (1) | CN1753878A (pt) |
| AR (1) | AR043205A1 (pt) |
| AU (1) | AU2003290032B2 (pt) |
| BR (1) | BR0318125A (pt) |
| CA (1) | CA2516467A1 (pt) |
| CR (1) | CR7937A (pt) |
| DE (1) | DE10307759B3 (pt) |
| EC (1) | ECSP056026A (pt) |
| MX (1) | MXPA05008781A (pt) |
| NO (1) | NO20054291L (pt) |
| RU (1) | RU2005128834A (pt) |
| WO (1) | WO2004074267A1 (pt) |
| ZA (1) | ZA200507437B (pt) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| DE102004023093B3 (de) * | 2004-05-05 | 2006-03-02 | Schering Ag | Trimere makrocyclisch substituierte Halogen-Benzolderivate |
| DE102004026103A1 (de) * | 2004-05-25 | 2005-12-22 | Schering Ag | Trimere makrocyclisch substituierte Aminoisophthalsäure-Halogen-Benzolderivate |
| ES2257152B1 (es) * | 2004-05-31 | 2007-07-01 | Laboratorios Almirall S.A. | Combinaciones que comprenden agentes antimuscarinicos y agonistas beta-adrenergicos. |
| DE102007058220A1 (de) | 2007-12-03 | 2009-06-04 | Bayer Schering Pharma Aktiengesellschaft | Dimere macrocyclisch substituierte Benzolderivate |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| CN103189057B (zh) * | 2010-08-26 | 2015-02-18 | 崔坤元 | 大环脂类化合物及其应用 |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| CN104721844B (zh) * | 2015-02-02 | 2017-11-03 | 湖北大学 | 一种新型ct，mri，稀土荧光三功能微球及其制备方法和应用 |
| CN104672259B (zh) * | 2015-02-02 | 2017-04-05 | 湖北大学 | 一种含碘稀土铕(ⅲ)配合物及其制备方法和应用 |
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| CN105254529B (zh) * | 2015-09-21 | 2017-05-31 | 西南石油大学 | 一种树形席夫碱缓蚀剂的制备方法 |
| CN110035996B (zh) | 2016-11-28 | 2022-08-09 | 拜耳医药股份公司 | 用于磁共振成像的新型高弛豫性钆螯合物 |
| CN107445911B (zh) * | 2017-06-19 | 2019-07-05 | 南京科技职业学院 | 一种二核含钆磁共振对比剂及其制备与应用 |
| KR20210095168A (ko) | 2018-11-23 | 2021-07-30 | 바이엘 악티엔게젤샤프트 | 조영 매체의 제형 및 그의 제조 방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5324503A (en) * | 1992-02-06 | 1994-06-28 | Mallinckrodt Medical, Inc. | Iodo-phenylated chelates for x-ray contrast |
| AU6996594A (en) * | 1993-06-02 | 1994-12-20 | Bracco S.P.A. | Iodinated paramagnetic chelates, and their use as contrast agents |
| FR2736051B3 (fr) * | 1995-06-29 | 1997-09-26 | Guerbet Sa | Complexes metalliques de polyaminoacides, leur procede de preparation et leur utilisation en imagerie diagnostique |
| FR2793795B1 (fr) * | 1999-05-21 | 2001-08-03 | Guerbet Sa | Isomeres de tetramides du complexe de gadolinium de l'acide (1,4,7,10-tetrazacyclododecane)1,4,7,10-tetra(2-glutarique) leur procede de preparation et leur application en imagerie medicale |
| FR2794744B1 (fr) * | 1999-06-09 | 2001-09-21 | Guerbet Sa | Complexes metalliques de polyaminoacides bicycliques, leur procede de preparation et leur application en imagerie medicale |
-
2003
- 2003-02-19 DE DE10307759A patent/DE10307759B3/de not_active Expired - Fee Related
- 2003-12-12 CA CA002516467A patent/CA2516467A1/en not_active Abandoned
- 2003-12-12 JP JP2004568408A patent/JP2006514664A/ja not_active Withdrawn
- 2003-12-12 RU RU2005128834/04A patent/RU2005128834A/ru not_active Application Discontinuation
- 2003-12-12 AU AU2003290032A patent/AU2003290032B2/en not_active Expired - Fee Related
- 2003-12-12 WO PCT/EP2003/014149 patent/WO2004074267A1/de active Application Filing
- 2003-12-12 EP EP03782386A patent/EP1594851A1/de not_active Withdrawn
- 2003-12-12 BR BR0318125-1A patent/BR0318125A/pt not_active IP Right Cessation
- 2003-12-12 KR KR1020057015199A patent/KR20050105474A/ko not_active Application Discontinuation
- 2003-12-12 CN CNA2003801098702A patent/CN1753878A/zh active Pending
- 2003-12-12 MX MXPA05008781A patent/MXPA05008781A/es active IP Right Grant
-
2004
- 2004-02-18 AR ARP040100490A patent/AR043205A1/es unknown
-
2005
- 2005-08-09 CR CR7937A patent/CR7937A/es not_active Application Discontinuation
- 2005-09-15 ZA ZA200507437A patent/ZA200507437B/en unknown
- 2005-09-16 NO NO20054291A patent/NO20054291L/no not_active Application Discontinuation
- 2005-09-19 EC EC2005006026A patent/ECSP056026A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004074267A1 (de) | 2004-09-02 |
| CN1753878A (zh) | 2006-03-29 |
| DE10307759B3 (de) | 2004-11-18 |
| AR043205A1 (es) | 2005-07-20 |
| AU2003290032B2 (en) | 2009-04-23 |
| EP1594851A1 (de) | 2005-11-16 |
| CA2516467A1 (en) | 2004-09-02 |
| AU2003290032A1 (en) | 2004-09-09 |
| NO20054291D0 (no) | 2005-09-16 |
| JP2006514664A (ja) | 2006-05-11 |
| NO20054291L (no) | 2005-11-17 |
| KR20050105474A (ko) | 2005-11-04 |
| CR7937A (es) | 2006-02-07 |
| MXPA05008781A (es) | 2006-03-10 |
| ECSP056026A (es) | 2006-01-27 |
| RU2005128834A (ru) | 2006-03-20 |
| BR0318125A (pt) | 2006-02-07 |
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