NO327490B1 - Isoftalamid derivat som gul polymorf - Google Patents
Isoftalamid derivat som gul polymorf Download PDFInfo
- Publication number
- NO327490B1 NO327490B1 NO19995676A NO995676A NO327490B1 NO 327490 B1 NO327490 B1 NO 327490B1 NO 19995676 A NO19995676 A NO 19995676A NO 995676 A NO995676 A NO 995676A NO 327490 B1 NO327490 B1 NO 327490B1
- Authority
- NO
- Norway
- Prior art keywords
- isophthalamide
- dihydroxypropyl
- bis
- triiodo
- amino
- Prior art date
Links
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical class NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 title description 2
- KAEGSAWWVYMWIQ-UHFFFAOYSA-N 5-amino-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I KAEGSAWWVYMWIQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 238000002329 infrared spectrum Methods 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 229960001025 iohexol Drugs 0.000 claims description 6
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- AMDBBAQNWSUWGN-UHFFFAOYSA-N Ioversol Chemical compound OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I AMDBBAQNWSUWGN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002872 contrast media Substances 0.000 claims description 4
- 229960004537 ioversol Drugs 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 229960004359 iodixanol Drugs 0.000 claims description 3
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 claims description 3
- 229960000780 iomeprol Drugs 0.000 claims description 3
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 claims description 3
- 229960000824 iopentol Drugs 0.000 claims description 3
- IUNJANQVIJDFTQ-UHFFFAOYSA-N iopentol Chemical compound COCC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I IUNJANQVIJDFTQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- IIHOIAOMFRCCKR-UHFFFAOYSA-N 2-(2,3-dihydroxypropyl)benzene-1,3-dicarboxamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1CC(O)CO IIHOIAOMFRCCKR-UHFFFAOYSA-N 0.000 claims 6
- 229940126062 Compound A Drugs 0.000 description 28
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- -1 2,3-dihydroxypropyl Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DEDJYTUBDONCKY-UHFFFAOYSA-N 4,6-bis(2,3-dihydroxypropyl)benzene-1,3-dicarboxamide Chemical compound OC(CC1=CC(=C(C=C1C(=O)N)C(=O)N)CC(CO)O)CO DEDJYTUBDONCKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012045 crude solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GNBBCFFLJFKAHB-UHFFFAOYSA-N 5-amino-1-n,3-n-bis(2,3-dihydroxypropyl)benzene-1,3-dicarboxamide;hydrochloride Chemical class Cl.NC1=CC(C(=O)NCC(O)CO)=CC(C(=O)NCC(O)CO)=C1 GNBBCFFLJFKAHB-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 210000004913 chyme Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-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
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- 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
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Steroid Compounds (AREA)
- Polyamides (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9710726.2A GB9710726D0 (en) | 1997-05-23 | 1997-05-23 | Compound |
| PCT/GB1998/001492 WO1998052911A1 (en) | 1997-05-23 | 1998-05-22 | Yellow polymorph of 5-amino-2,4,6-triiodo-n,n'-bis(2,3-dihydroxypropyl)-isophthalamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995676D0 NO995676D0 (no) | 1999-11-19 |
| NO995676L NO995676L (no) | 1999-11-19 |
| NO327490B1 true NO327490B1 (no) | 2009-07-13 |
Family
ID=10812988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995676A NO327490B1 (no) | 1997-05-23 | 1999-11-19 | Isoftalamid derivat som gul polymorf |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6337422B1 (de) |
| EP (1) | EP0983230B1 (de) |
| JP (1) | JP4476366B2 (de) |
| KR (1) | KR100543856B1 (de) |
| CN (1) | CN1161324C (de) |
| AT (1) | ATE256101T1 (de) |
| AU (1) | AU725565B2 (de) |
| BR (1) | BRPI9809153B8 (de) |
| CA (1) | CA2290544A1 (de) |
| CZ (1) | CZ297243B6 (de) |
| DE (1) | DE69820435T2 (de) |
| GB (1) | GB9710726D0 (de) |
| HU (1) | HU224128B1 (de) |
| IL (1) | IL133100A (de) |
| NO (1) | NO327490B1 (de) |
| PL (1) | PL190905B1 (de) |
| PT (1) | PT983230E (de) |
| WO (1) | WO1998052911A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7524515B2 (en) * | 2003-01-10 | 2009-04-28 | Mutual Pharmaceuticals, Inc. | Pharmaceutical safety dosage forms |
| EP1989179B1 (de) | 2006-02-15 | 2011-01-26 | Ge Healthcare As | Kontrastmittel |
| US7662859B2 (en) | 2007-02-16 | 2010-02-16 | Ge Healthcare As | Contrast agents |
| US20110256068A1 (en) | 2009-01-09 | 2011-10-20 | Wistand Lars-Goeran | Contrast media compositions |
| US20110021834A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | Continuous process of preparing intermediate for non-ionic x-ray contrast agents |
| EP2281807A1 (de) * | 2009-07-21 | 2011-02-09 | GE Healthcare AS | Entfärben von 5-amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamid, ein Kontrastmittelzwischenprodukt |
| US20110021833A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | Crystallization of an intermediate for synthesizing non-ionic x-ray contrast agents |
| ES2887104T3 (es) | 2011-09-19 | 2021-12-21 | Orexo Ab | Comprimidos sublinguales resistentes al abuso que comprenden buprenorfina y naloxona |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1548594A (en) * | 1976-06-11 | 1979-07-18 | Nyegaard & Co As | Triiodoisophthalic acid amides |
| US4256729A (en) * | 1979-03-23 | 1981-03-17 | Mallinckrodt, Inc. | N,N'-Bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-keto-L-gulonamido)isophthalamide and radiological compositions containing same |
| US4396598A (en) * | 1982-01-11 | 1983-08-02 | Mallinckrodt, Inc. | Triiodoisophthalamide X-ray contrast agent |
| AU612510B2 (en) * | 1988-03-01 | 1991-07-11 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| US5013865A (en) * | 1988-04-06 | 1991-05-07 | Mallinckrodt, Inc. | Process for the preparation of 2,4,6-triiodo-5-amino-N-alkylisophthalamic acid and 2,4,6-triiodo-5-amino-isophthalamide compounds |
| US5256393A (en) * | 1991-04-16 | 1993-10-26 | Mallinckrodt Medical, Inc. | Use of azeotropic distillation in process to dry 5-amino-N,N'bis (2,3-dihydroxypropyl)-2,4,6-triiodoisphthalamide |
| EP0762900B1 (de) * | 1994-06-21 | 2001-11-21 | Mallinckrodt Inc. | Verbesserte synthese von ioversol unter verwendung einer mit phosphorsäure modifizierten koaddition |
| GB9419206D0 (en) * | 1994-09-23 | 1994-11-09 | Nycomed Innovation Ab | Contrast media |
| DE69609963T2 (de) * | 1995-05-24 | 2001-04-12 | Nycomed Imaging As | Verfahren zur iodierung |
-
1997
- 1997-05-23 GB GBGB9710726.2A patent/GB9710726D0/en active Pending
-
1998
- 1998-05-22 CA CA002290544A patent/CA2290544A1/en not_active Abandoned
- 1998-05-22 WO PCT/GB1998/001492 patent/WO1998052911A1/en active IP Right Grant
- 1998-05-22 AU AU75407/98A patent/AU725565B2/en not_active Ceased
- 1998-05-22 IL IL13310098A patent/IL133100A/en not_active IP Right Cessation
- 1998-05-22 DE DE69820435T patent/DE69820435T2/de not_active Expired - Lifetime
- 1998-05-22 EP EP98922947A patent/EP0983230B1/de not_active Expired - Lifetime
- 1998-05-22 CZ CZ0417199A patent/CZ297243B6/cs not_active IP Right Cessation
- 1998-05-22 PT PT98922947T patent/PT983230E/pt unknown
- 1998-05-22 PL PL336848A patent/PL190905B1/pl unknown
- 1998-05-22 HU HU0003637A patent/HU224128B1/hu active IP Right Grant
- 1998-05-22 AT AT98922947T patent/ATE256101T1/de active
- 1998-05-22 JP JP55014098A patent/JP4476366B2/ja not_active Expired - Lifetime
- 1998-05-22 KR KR1019997010757A patent/KR100543856B1/ko not_active IP Right Cessation
- 1998-05-22 CN CNB988053217A patent/CN1161324C/zh not_active Expired - Lifetime
- 1998-05-22 BR BRPI9809153-0 patent/BRPI9809153B8/pt not_active IP Right Cessation
-
1999
- 1999-11-12 US US09/438,385 patent/US6337422B1/en not_active Expired - Lifetime
- 1999-11-19 NO NO19995676A patent/NO327490B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0003637A3 (en) | 2001-06-28 |
| PL190905B1 (pl) | 2006-02-28 |
| AU7540798A (en) | 1998-12-11 |
| PL336848A1 (en) | 2000-07-17 |
| KR100543856B1 (ko) | 2006-01-23 |
| EP0983230B1 (de) | 2003-12-10 |
| DE69820435D1 (en) | 2004-01-22 |
| DE69820435T2 (de) | 2004-10-07 |
| BRPI9809153B8 (pt) | 2021-07-06 |
| ATE256101T1 (de) | 2003-12-15 |
| JP2001526678A (ja) | 2001-12-18 |
| HUP0003637A1 (hu) | 2001-02-28 |
| IL133100A0 (en) | 2001-03-19 |
| CN1257479A (zh) | 2000-06-21 |
| BRPI9809153A (pt) | 2000-08-01 |
| GB9710726D0 (en) | 1997-07-16 |
| CN1161324C (zh) | 2004-08-11 |
| US6337422B1 (en) | 2002-01-08 |
| KR20010012794A (ko) | 2001-02-26 |
| EP0983230A1 (de) | 2000-03-08 |
| NO995676D0 (no) | 1999-11-19 |
| NO995676L (no) | 1999-11-19 |
| IL133100A (en) | 2004-07-25 |
| WO1998052911A1 (en) | 1998-11-26 |
| BRPI9809153B1 (pt) | 2017-11-14 |
| CZ417199A3 (cs) | 2000-05-17 |
| PT983230E (pt) | 2004-04-30 |
| CA2290544A1 (en) | 1998-11-26 |
| HU224128B1 (hu) | 2005-05-30 |
| JP4476366B2 (ja) | 2010-06-09 |
| AU725565B2 (en) | 2000-10-12 |
| CZ297243B6 (cs) | 2006-10-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |