CA1053693A - L'acide 2,4,6-triiodo-5-methoxyacetamido-n-methylisophthalamique, ses sels, ses halogenures d'acyle et ses esters - Google Patents

L'acide 2,4,6-triiodo-5-methoxyacetamido-n-methylisophthalamique, ses sels, ses halogenures d'acyle et ses esters

Info

Publication number: CA1053693A
Authority: CA; Canada
Prior art keywords: triiodo; methoxyacetamido; acid; solution; methylisophthalamic
Prior art date: 1975-09-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA235,283A

Other languages

English (en)

Inventor

Philip E. Wiegert

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mallinckrodt Chemical Inc

Original Assignee

Mallinckrodt Chemical Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-09-11

Filing date

1975-09-11

Publication date

1979-05-01

1975-09-11 Application filed by Mallinckrodt Chemical Inc filed Critical Mallinckrodt Chemical Inc

1975-09-11 Priority to CA235,283A priority Critical patent/CA1053693A/fr

1979-05-01 Application granted granted Critical

1979-05-01 Publication of CA1053693A publication Critical patent/CA1053693A/fr

Status Expired legal-status Critical Current

Links

RQWSRKPCQRIHNQ-UHFFFAOYSA-N 2,4,6-triiodo-3-[(2-methoxyacetyl)amino]-5-(methylcarbamoyl)benzoic acid Chemical compound CNC(=O)C1=C(I)C(NC(=O)COC)=C(I)C(C(O)=O)=C1I RQWSRKPCQRIHNQ-UHFFFAOYSA-N 0.000 title claims abstract description 15
150000003839 salts Chemical class 0.000 title claims abstract description 13
150000001266 acyl halides Chemical class 0.000 title claims abstract description 7
150000002148 esters Chemical class 0.000 title claims abstract description 6
238000000034 method Methods 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 15
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 12
-1 haloacetyl halide Chemical class 0.000 claims description 10
229960003194 meglumine Drugs 0.000 claims description 6
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 claims description 4
AKXKBAWZIVNNJR-UHFFFAOYSA-N 3-amino-2,4,6-triiodo-5-(methylcarbamoyl)benzoic acid Chemical compound CNC(=O)C1=C(I)C(N)=C(I)C(C(O)=O)=C1I AKXKBAWZIVNNJR-UHFFFAOYSA-N 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
GJWVFYSVIXJJKI-UHFFFAOYSA-N 2,4,6-triiodo-3-[(2-methoxyacetyl)amino]-5-(methylcarbamoyl)benzoyl chloride Chemical compound CNC(=O)C1=C(I)C(NC(=O)COC)=C(I)C(C(Cl)=O)=C1I GJWVFYSVIXJJKI-UHFFFAOYSA-N 0.000 claims description 3
ZLOVBNZJWKBSBX-UHFFFAOYSA-N ethyl 2,4,6-triiodo-3-[(2-methoxyacetyl)amino]-5-(methylcarbamoyl)benzoate Chemical compound CCOC(=O)C1=C(I)C(NC(=O)COC)=C(I)C(C(=O)NC)=C1I ZLOVBNZJWKBSBX-UHFFFAOYSA-N 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
239000002872 contrast media Substances 0.000 abstract description 7
239000000543 intermediate Substances 0.000 abstract description 5
239000000243 solution Substances 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000002253 acid Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
UXIGWFXRQKWHHA-UHFFFAOYSA-N Iotalamic acid Chemical compound CNC(=O)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I UXIGWFXRQKWHHA-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000002002 slurry Substances 0.000 description 5
231100000419 toxicity Toxicity 0.000 description 5
230000001988 toxicity Effects 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000011630 iodine Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000906446 Theraps Species 0.000 description 3
229940039231 contrast media Drugs 0.000 description 3
238000007865 diluting Methods 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
229960000929 iotalamic acid Drugs 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
FVUKYCZRWSQGAS-UHFFFAOYSA-N 3-carbamoylbenzoic acid Chemical class NC(=O)C1=CC=CC(C(O)=O)=C1 FVUKYCZRWSQGAS-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
SHWNNYZBHZIQQV-UHFFFAOYSA-L calcium;disodium;2-[2-[bis(carboxylatomethyl)azaniumyl]ethyl-(carboxylatomethyl)azaniumyl]acetate Chemical compound [Na+].[Na+].[Ca+2].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O SHWNNYZBHZIQQV-UHFFFAOYSA-L 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000007429 general method Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910000403 monosodium phosphate Inorganic materials 0.000 description 2
235000019799 monosodium phosphate Nutrition 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000003880 polar aprotic solvent Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
XJCRPROBEGKITL-UHFFFAOYSA-N 3-acetamido-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]benzoic acid Chemical compound COCC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I XJCRPROBEGKITL-UHFFFAOYSA-N 0.000 description 1
DLTCLUPPEMEAGB-UHFFFAOYSA-N 3-carbamoyl-2,4,6-triiodobenzoic acid Chemical class NC(=O)C1=C(I)C=C(I)C(C(O)=O)=C1I DLTCLUPPEMEAGB-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
241000518994 Conta Species 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
RXDLGFMMQFNVLI-UHFFFAOYSA-N [Na].[Na].[Ca] Chemical compound [Na].[Na].[Ca] RXDLGFMMQFNVLI-UHFFFAOYSA-N 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000011955 best available control technology Methods 0.000 description 1
LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
229940052299 calcium chloride dihydrate Drugs 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
229940009662 edetate Drugs 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229940029378 iothalamate Drugs 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
229940091250 magnesium supplement Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
MNDFXDXRMYURMC-UHFFFAOYSA-N methyl 3-carbamoylbenzoate Chemical compound COC(=O)C1=CC=CC(C(N)=O)=C1 MNDFXDXRMYURMC-UHFFFAOYSA-N 0.000 description 1
RAYLUPYCGGKXQO-UHFFFAOYSA-N n,n-dimethylacetamide;hydrate Chemical compound O.CN(C)C(C)=O RAYLUPYCGGKXQO-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
SHYRYRFMXQIDLU-UHFFFAOYSA-M sodium;2,4,6-triiodo-3-[(2-methoxyacetyl)amino]-5-(methylcarbamoyl)benzoate Chemical compound [Na+].CNC(=O)C1=C(I)C(NC(=O)COC)=C(I)C(C([O-])=O)=C1I SHYRYRFMXQIDLU-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
238000007487 urography Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Landscapes

Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA235,283A 1975-09-11 1975-09-11 L'acide 2,4,6-triiodo-5-methoxyacetamido-n-methylisophthalamique, ses sels, ses halogenures d'acyle et ses esters Expired CA1053693A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA235,283A CA1053693A (fr)	1975-09-11	1975-09-11	L'acide 2,4,6-triiodo-5-methoxyacetamido-n-methylisophthalamique, ses sels, ses halogenures d'acyle et ses esters

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA235,283A CA1053693A (fr)	1975-09-11	1975-09-11	L'acide 2,4,6-triiodo-5-methoxyacetamido-n-methylisophthalamique, ses sels, ses halogenures d'acyle et ses esters

Publications (1)

Publication Number	Publication Date
CA1053693A true CA1053693A (fr)	1979-05-01

Family

ID=4104030

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA235,283A Expired CA1053693A (fr)	1975-09-11	1975-09-11	L'acide 2,4,6-triiodo-5-methoxyacetamido-n-methylisophthalamique, ses sels, ses halogenures d'acyle et ses esters

Country Status (1)

Country	Link
CA (1)	CA1053693A (fr)

1975
- 1975-09-11 CA CA235,283A patent/CA1053693A/fr not_active Expired

Publication	Publication Date	Title
CA1130316A (fr)	1982-08-24	Diamides d'acide isophtalique tri-iodes utilises comme agents de contraste non ioniques pour rayons x
US5621000A (en)	1997-04-15	Nitric esters having a pharmacological activity and process for their preparation
US4160015A (en)	1979-07-03	2,4,6-Triiodobenzoic acid derivatives and their use as x-ray contrast agents
US3097228A (en)	1963-07-09	Derivatives of 2, 4, 6-trhodobenzoyloxyalkanoic acids and preparation thereof
HU176251B (en)	1981-01-28	Process for producing 2,4,6-triiodo-benzoic acid derivatives substituted with 2,4,6-triiodo-benzoyl-amino-alkyl-acetamido group
DE19508058A1 (de)	1996-08-22	Verfahren zur Herstellung von DTPA-Tetraestern der terminalen Carbonsäuren und deren Verwendung zur Herstellung pharmazeutischer Mittel
JPH01503786A (ja)	1989-12-21	プロスタグランジン誘導体，それらの製法及びそれらを含有する医薬組成物
US4066743A (en)	1978-01-03	X-ray contrast agents
US3953497A (en)	1976-04-27	2,4,6-Triiodo-5-methoxyacetamido-N-methylisophthalamic acid and salts, acyl halides and esters thereof
DD282691A5 (de)	1990-09-19	Verfahren zur herstellung von cephalosporin
DE2225694B2 (de)	1975-04-10	Cephalosporinverbindungen und Verfahren zu deren Herstellung
DE2653635C2 (de)	1986-10-02	&alpha;-Aminoketonderivate, deren Herstellung und pharmazeutische Zusammensetzungen auf deren Basis
US4069250A (en)	1978-01-17	Substituted 2,4,6-triiodoisophthalamic acids
CA1053693A (fr)	1979-05-01	L'acide 2,4,6-triiodo-5-methoxyacetamido-n-methylisophthalamique, ses sels, ses halogenures d'acyle et ses esters
DE3215676C2 (de)	1984-02-16	Amidinderivate, Verfahren zu deren Herstellung und pharmazeutische Mittel, die diese Verbindungen enthalten
DE2446100C3 (de)	1982-01-14	Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel
DE3037284C2 (de)	1984-04-12	Penicillinverbindungen und Verfahren zu deren Herstellung, sowie Arzneimittel, welche diese enthalten
US4138589A (en)	1979-02-06	Substituted isophthalamic acids
US4018783A (en)	1977-04-19	Esters of metrizoic acid
DE3222779C2 (fr)	1991-01-03
DE2325498A1 (de)	1973-12-06	Penicillinverbindungen und verfahren zu ihrer herstellung
US4321368A (en)	1982-03-23	Glycosyl triidobenzoic acid derivatives
US3359278A (en)	1967-12-19	Nu-substituted-2, 4, 6-triiodoanilic acids and salts thereof
EP0155006B1 (fr)	1990-10-24	Composés à activité antibactérienne, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0647618B1 (fr)	1997-01-02	Nouveaux dimeres iodes non-ioniques utiles comme agents de contraste aux rayons x, procede de preparation de ces nouveaux dimeres, et compositions galeniques les contenant