NO148811B - Utgangsmateriale for fremstilling av nye dicarboxylsyre-bis-(3,5-dicarbamoyl-2,4,6-trijodanilider) - Google Patents
Utgangsmateriale for fremstilling av nye dicarboxylsyre-bis-(3,5-dicarbamoyl-2,4,6-trijodanilider) Download PDFInfo
- Publication number
- NO148811B NO148811B NO822674A NO822674A NO148811B NO 148811 B NO148811 B NO 148811B NO 822674 A NO822674 A NO 822674A NO 822674 A NO822674 A NO 822674A NO 148811 B NO148811 B NO 148811B
- Authority
- NO
- Norway
- Prior art keywords
- bis
- acid
- chlorocarbonyl
- starting material
- triiodo
- Prior art date
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000463 material Substances 0.000 title description 2
- 239000007858 starting material Substances 0.000 claims description 7
- BMKKXMYQHGGGDS-UHFFFAOYSA-N 5-[[2-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-2-oxoacetyl]amino]-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C=1C(=C(NC(C(=O)NC2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I)=O)C(=C(C=1I)C(=O)Cl)I)I BMKKXMYQHGGGDS-UHFFFAOYSA-N 0.000 claims description 3
- VBTGFQLGRMQVTN-UHFFFAOYSA-N 5-[[3-(3,5-dicarbonochloridoyl-2,4,6-triiodo-N-methylanilino)-3-oxopropanoyl]-methylamino]-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound CN(C(=O)CC(=O)N(C)C1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I)C1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I VBTGFQLGRMQVTN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- RVQWKSZZWPFNAD-UHFFFAOYSA-N 5-[[6-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-6-oxohexanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C=1C(=C(NC(CCCCC(=O)NC2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I)=O)C(=C(C=1I)C(=O)Cl)I)I RVQWKSZZWPFNAD-UHFFFAOYSA-N 0.000 claims description 2
- FGCGGWJXZPMUPL-UHFFFAOYSA-N [3-(3,5-dicarbonochloridoyl-2,4,6-triiodo-N-methylanilino)-3-oxopropyl] N-(3,5-dicarbonochloridoyl-2,4,6-triiodophenyl)-N-methylcarbamate Chemical compound ClC(=O)C=1C(=C(N(C(OCCC(=O)N(C2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I)C)=O)C)C(=C(C=1I)C(=O)Cl)I)I FGCGGWJXZPMUPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002872 contrast media Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- JSZGHINQSIMICA-UHFFFAOYSA-N CC(C(=O)NC1=C(C(=C(C(=C1I)C(=O)Cl)I)C(=O)Cl)I)C(=O)NC2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I Chemical compound CC(C(=O)NC1=C(C(=C(C(=C1I)C(=O)Cl)I)C(=O)Cl)I)C(=O)NC2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I JSZGHINQSIMICA-UHFFFAOYSA-N 0.000 description 2
- WDRKKEQVQCRJMS-UHFFFAOYSA-N ClC(=O)C=1C(=C(N(C(CCC(=O)N(C2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I)C)=O)C)C(=C(C1I)C(=O)Cl)I)I Chemical compound ClC(=O)C=1C(=C(N(C(CCC(=O)N(C2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I)C)=O)C)C(=C(C1I)C(=O)Cl)I)I WDRKKEQVQCRJMS-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DPLMHGOPFZLSRR-UHFFFAOYSA-N (3-chloro-3-oxopropyl) carbonochloridate Chemical compound ClC(=O)CCOC(Cl)=O DPLMHGOPFZLSRR-UHFFFAOYSA-N 0.000 description 1
- QMADWSQEVHUFFJ-UHFFFAOYSA-N 2,4,5-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(I)=C(I)C(C(O)=O)=C1I QMADWSQEVHUFFJ-UHFFFAOYSA-N 0.000 description 1
- TZEBLZRSPJJCOS-UHFFFAOYSA-N 2,4,6-triiodo-5-(methylamino)benzene-1,3-dicarbonyl chloride Chemical compound CNC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I TZEBLZRSPJJCOS-UHFFFAOYSA-N 0.000 description 1
- IEEHKTFVUIVORU-UHFFFAOYSA-N 2-methylpropanedioyl dichloride Chemical compound ClC(=O)C(C)C(Cl)=O IEEHKTFVUIVORU-UHFFFAOYSA-N 0.000 description 1
- OFJRMOPEXAYEMU-UHFFFAOYSA-N CC(CCC(=O)NC1=C(C(=C(C(=C1I)C(=O)Cl)I)C(=O)Cl)I)CC(=O)NC2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I Chemical compound CC(CCC(=O)NC1=C(C(=C(C(=C1I)C(=O)Cl)I)C(=O)Cl)I)CC(=O)NC2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I OFJRMOPEXAYEMU-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
Foreliggende oppfinnelse angår som angitt i krav 1 ut^-gangsmaterialer for fremstilling av materialer for anvendelse som røntgenkontrastmidler hvis fremstilling og egenskaper fremgår av norsk patent 147.447.
Tetracarboxylsyretetrakloridene ifølge oppfinnelsen med den generelle formel II kan fremstilles ved at man på kjent vis om-setter et 2,4,6-trijodisofthalsyrediklorid med den generelle formel: hvor R3 er hydrogen eller methyl, med et dicarboxylsyreklorid med den generelle formel:
De nye forbindelser med formel II fåes fra de kjente 5-amino-, hhv. 5-alkylamino-2,4,6-trijodisofthalsyrediklorider ved kondensasjon med dikloridet av alifatisk dicarboxylsyre med formelen C1/C0-X-C0-C1, hvor X er som ovenfor angitt. Som reak-sjonsmedium er organiske oppløsningsmidler, f.eks. aromatiske hydrocarboner som klorbenzen og toluen, men særlig inerte polare oppløsningsmidler som dimethylacetamid, N-rinethylpyrrolidon, dioxan, tetrahydrofuran og andre egnet. Særlig foretrukne oppløsnings-midler er f.eks. dimethylacetamid, dioxan og tetrahydrofuran.
De ved omsetningen dannede dimere tetracarboxylsyretetra-klorider med den generelle formel II krystalliserer enten ut eller isoleres ved inndampning av oppløsningene i vakuum.
De etterfølgende eksempler tjener til ytterligere å belyse foreliggende opp finnelsesgjenstand.
Eksempel 1
Oxalsyre-di-( 3, 5-diklorcarbonyl-2 , 4 , 6-tri jodanilid)
En oppløsning av 103 g 5-amino-trijodisofthalsyrediklorid i 412 ml dioxan blir i et oljebad ved 80 - 90°C indre temperatur i løpet av 10 minutter tilsatt 10,3 ml oxalsyrediklorid dråpevis under omrøring. Efter 2 timers omrøring i varmen krystalliserer den nye forbindelse ut, og dette kan påskyndes ved kimtilsetning. Efter omrøring over natten ved værelsetemperatur avsuges bunnfallet og tørres under utelukkelse av fuktighet.
Utbytte av rått oxalsyre-di-(3,5-diklorcarbonyl-2,4,6-tri-jodanilid) er 88,5 g = 7 3,6% av det teoretiske under hensyntagen til et dioxaninnhold på 10 vekt%. Smp.; ingen spaltning inntil 320°C.
Eksempel 2
Oxaglutarsyre-bis-(3,5-bis^klorcarbonyl-2,4,6-trijod-N-methylanilid)
En oppløsning av 110 g 5-methylamino-2,4,6-trijodisofthalsyre-diklorid i 110 ml dioxan ble under omrøring ved 80°C dråpevis tilsatt 18,5 9 2-oxaglutarsyre-diklorid. Derpå ble reaksjonsblandingen kokt i 5,5 timer under tilbakeløp, hvor-under et bunnfall falt ut. Dette ble avsuget efter 20 timers omrøring.
Utbytte: 6o,5 g = 51% av det teoretiske oxaglutarsyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijod-N-methylanilid). Spaltning ved ca. 300°C, dioxaninnhold under 0,5%.
Beregnet Cl IO,76%, I 57,79%,
Funnet: Cl 11,3 %, I 57,7 %.
Eksempel 3
Malonsyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijod-N-methylanilid)
En oppløsning av 30,5 9 5-met hy lam ino-2 ,4, 6-t r i jodisof thai - syre-diklorid i 45 ml dioxan ble under tilbakeløp langsomt tilsatt 4,2 g malonylklorid og videre oppvarmet i 3 timer. Efter avkjøling ble bunnfallet avsuget.
Utbytte: 25,8 9 = 80% av det teoretiske av malonsyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijod-N-methylanilid). Dioxaninnhold 0,8%. Smeltepunkt over 300°C.
Eksempel 4
Adipinsyre^bis-(3,5-bis-klorcarbonyl-2,4,6-trijodanilid)
En oppløsning av 221 g 5-amino-trijodisofthalsyre-diklorid i 320 ml dioxan ble under tilbakeløp tildryppet 4l 9 adipinsyre-diklorid. Efter 3 timers oppvarmning og efter avkjøling over natten ble bunnfallet avsuget.
Utbytte: 169 9 = 67% av det teoretiske av adipinsyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijodanilid) med 6% dioxan,
spaltning fra 292°C.
Eksempel 5
3,6-dioxakorksyre-bis-(3,5-bis —klorcarbonyl-2,4,6-trijodanilid)
En oppløsning av 119 g 5-amino-trijodisofthalsyre-diklorid i 119 ml dioxan ble under tilbakeløp tildryppet 25,8 9 dioxa-korksyre-diklorid. Efter 6 timers oppvarmning og avkjøling over natten ble bunnfallet avsuget.
Utbytte: 75 g = 52% av det teoretiske av 3,6-dioxakorksyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijodanilid) med 6,8% dioxan, spaltning 260-262°C.
Eksempel 6
Ravsyre-bis-[3,5-bis-(klorcarbonyl)-2,4,6-trijod-N-methylanilid]
En oppløsning av 30,5 g methylamino-2,4,6-trijod-isofthal-syre-diklorid i 50 ml dioxan tilsettes under tilbakeløp langsomt 4,65 g ravsyre-diklorid og oppvarmes videre i 3 timer. Efter avkjøling avsuges bunnfallet.
Utbytte: 25,7 g (78% av det teoretiske) ravsyre-bis-[3,5-bis-(klorcarbonyl)-2,4,6-trijod-N-methylanilid] med et dioxaninnhold på 1% og smeltepunkt over 300°C.
Eksempel 7
Methylmalonsyre-bis-[3,5-bis-(klorcarbonyl)-2,4,6-trijodanilid]
En oppløsning av 29,8 g 5-amino-2,4,6,trijod-isofthalsyre-diklorid i 30 ml dioxan tilsettes under tilbakeløp lang-
somt 4,6 g methylmalonsyre-diklorid og oppvarmes videre i 4 timer. Efter avkjøling avsuges bunnfallet.
Utbytte: 13,8 g (40% av det teoretiske) methylmalonsyre-bis- [3 , 5-bis- (klorcarbonyl) -2 , 4 , 6-tri jodanilid] med et dioxaninnhold på 7,8% og smeltepunkt 278-280°C.
Eksempel 8
3-methyl-adipinsyre-bis-[3,5-bis-(klorcarbonyl)-2,4,6-trijodanilid]
En oppløsning av 29,8 g 5-amino-2,4,6-trijod-isofthalsyre-diklorid i 30 ml dioxan tilsettes under tilbakeløp lang-
somt 5,9 g DL-3-methyladipinsyre-diklorid og oppvarmes videre i 4 timer. Efter avkjøling avsuges bunnfallet.
Utbytte: 21,9 g (63% av det teoretiske) 3-methyl-adipinsyre-bis- [3,5-bis-(klorcarbonyl)-2,4,6-trijod-
anilid] , med et dioxaninnhold på 5,1%, smeltepunkt fra 274°C (spaltning).
Claims (6)
1. Utgangsmateriale for fremstilling av dicarboxylsyre-bis-(3,5-dicarbamoyl-2,4,6-trijodanilid) for anvendelse som røntgenkontrastmiddel, med den generelle formel:
hvor R. er en rettkjedet eller forgrenet mono- eller polyhydroxyalkylgruppe med 2-6 carbonatomer og 1-5 hydroxy-grupper, R_ er hydrogen eller alkyl med 1 eller 2 carbonatomer, som eventuelt kan være substituert med en hydroxy-gruppe, R^ er hydrogen eller methyl, og X er en direkte-binding eller (CH„) hvor n er 1-4, eller (CHo0CH„) hvor
zn z z n n er 1-3, eller
karakterisert ved at det er et carboxylsyre-tetraklorid med den generelle formel:
hvor R^ og X er som ovenfor angitt.
2. Utgangsmateriale karakterisert ved at det er: oxalsyre-bis-[3,5-bis-(klorcarbonyl)-2,4,6-trijodanilid].
3. Utgangsmateriale karakterisert ved at det er: oxaglutarsyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijod-N-methylanilid) .
4. Utgangsmateriale karakterisert ved at det er: malonsyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijod-N-methyl-anilid) .
5. Utgangsmateriale karakterisert ved at det er: adipinsyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijodanilid).
6. Utgangsmateriale karakterisert ved at det er: 3,6-dioxakorksyre-bis-(3,5-bis-klorcarbonyl-2,4,6-trijod-anilid) .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2628517A DE2628517C2 (de) | 1976-06-23 | 1976-06-23 | Dicarbonsäure-bis(3,5-dicarbamoyl-2,4,6-trijodanilid)-Verbindungen, Verfahren zu ihrer Herstellung und Röntgenkontrastmittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO822674L NO822674L (no) | 1977-12-27 |
| NO148811B true NO148811B (no) | 1983-09-12 |
| NO148811C NO148811C (no) | 1983-12-21 |
Family
ID=5981407
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO772202A NO147447C (no) | 1976-06-23 | 1977-06-22 | Nye dicarboxylsyre-bis-(3,5-dicarbamoyl-2,4,6-trijodanilider) for anvendelse som skyggegivende komponent i roentgenkontrastmidler og roentgenkontrastmiddel inneholdende samme forbindelser |
| NO822674A NO148811C (no) | 1976-06-23 | 1982-08-04 | Utgangsmateriale for fremstilling av nye dicarboxylsyre-bis-(3,5-dicarbamoyl-2,4,6-trijodanilider) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO772202A NO147447C (no) | 1976-06-23 | 1977-06-22 | Nye dicarboxylsyre-bis-(3,5-dicarbamoyl-2,4,6-trijodanilider) for anvendelse som skyggegivende komponent i roentgenkontrastmidler og roentgenkontrastmiddel inneholdende samme forbindelser |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4239747A (no) |
| JP (2) | JPS537637A (no) |
| AT (1) | AT361117B (no) |
| AU (1) | AU512304B2 (no) |
| BE (1) | BE856039A (no) |
| CA (2) | CA1106400A (no) |
| CH (1) | CH629751A5 (no) |
| CS (1) | CS199680B2 (no) |
| DD (1) | DD131014A5 (no) |
| DE (1) | DE2628517C2 (no) |
| DK (2) | DK150505C (no) |
| ES (1) | ES460007A1 (no) |
| FI (1) | FI67540C (no) |
| FR (1) | FR2355808A1 (no) |
| GB (2) | GB1588733A (no) |
| GR (1) | GR71696B (no) |
| HU (1) | HU174228B (no) |
| IE (2) | IE45225B1 (no) |
| IL (2) | IL52356A (no) |
| IT (1) | IT1237314B (no) |
| LU (2) | LU77588A1 (no) |
| NL (1) | NL189510C (no) |
| NO (2) | NO147447C (no) |
| PL (1) | PL108102B1 (no) |
| PT (1) | PT66690B (no) |
| SE (1) | SE436871B (no) |
| SU (1) | SU917696A3 (no) |
| ZA (1) | ZA773782B (no) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH626873A5 (no) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa | |
| DK273280A (da) * | 1979-06-28 | 1980-12-29 | Schering Ag | Trijoderede 5-aminoisophthalsyrederivater |
| IT1193211B (it) * | 1979-08-09 | 1988-06-15 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono |
| IT1207226B (it) * | 1979-08-09 | 1989-05-17 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico, metodo per la loro preparazione e mezzi di contrasto che li contengono. |
| US4341756A (en) * | 1980-01-31 | 1982-07-27 | The Regents Of The University Of California | Novel amino-dioxepane intermediates for the synthesis of new non-ionic contrast media |
| JPS56127373A (en) * | 1980-01-31 | 1981-10-06 | Univ California | Novel amino-dioxepane intermediate for synthesizing novel nonionic contrast agent |
| DE3038853A1 (de) * | 1980-10-10 | 1982-05-27 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue n-hydroxy-alkylierte dicarbonsaeure-bis-(3,5-dicarbamoyl-2,4,6-trijodanilide), deren herstellung und diese enthaltende roentgenkonstrastmittel (ii) |
| ATE20733T1 (de) * | 1982-11-08 | 1986-08-15 | Nyegaard & Co As | Roentgenkontrastmittel. |
| FR2541272A1 (fr) * | 1983-02-23 | 1984-08-24 | Guerbet Sa | Composes bromes et produits opacifiants en contenant |
| US4650903A (en) * | 1984-06-21 | 1987-03-17 | The Bf Goodrich Company | Oligomeric amides as synergists for antioxidants and UV stabilizers |
| DE3731542A1 (de) * | 1987-09-17 | 1989-03-30 | Schering Ag | Neue dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6-triiod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
| DE3739098A1 (de) * | 1987-11-16 | 1989-05-24 | Schering Ag | Neue substituierte dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6- trijod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
| US5075502A (en) * | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| IT1252180B (it) * | 1991-12-10 | 1995-06-05 | Bracco Ind Chimica Spa | 5,5'-(1,3-propandiil) bis (imino (2-osso-2,1-etandiil)acetilimino)-bis(2,4,6-triiodo-1,3-benzendicarbossiamidi),loro metodo di preparazione e mezzi di contrasto roentgenografici che li contengono |
| CN1038725C (zh) * | 1993-12-04 | 1998-06-17 | 吉林省鹊源国际生物工程有限公司 | 复方天然香菇营养液 |
| US6149891A (en) * | 1995-05-31 | 2000-11-21 | Israel Humanitarian Foundation Ltd. | X-ray contrast medium and method for protecting against harmful effects thereof |
| IT1299202B1 (it) * | 1998-05-08 | 2000-02-29 | Dibra Spa | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
| US7790141B2 (en) * | 2003-08-11 | 2010-09-07 | Pathak Holdings, Llc | Radio-opaque compounds, compositions containing same and methods of their synthesis and use |
| EP2178568B1 (en) | 2007-07-12 | 2014-07-02 | Ge Healthcare As | Contrast agents |
| WO2009047318A1 (en) | 2007-10-12 | 2009-04-16 | Ge Healthcare As | Contrast agents |
| JP2011500533A (ja) | 2007-10-12 | 2011-01-06 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| JP2011500530A (ja) | 2007-10-12 | 2011-01-06 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| EP2200971B1 (en) | 2007-10-12 | 2013-04-24 | GE Healthcare AS | Contrast agents |
| WO2009056555A1 (en) * | 2007-10-30 | 2009-05-07 | Ge Healthcare As | Contrast agents |
| EP2240432B1 (en) * | 2008-01-14 | 2012-07-04 | Mallinckrodt LLC | Process for the preparation of iosimenol |
| WO2012136813A2 (en) | 2011-04-07 | 2012-10-11 | Universitetet I Oslo | Agents for medical radar diagnosis |
| WO2016079330A1 (en) | 2014-11-21 | 2016-05-26 | Technical University Of Denmark | Gel formulations for local drug release |
| MX2018014087A (es) | 2016-05-20 | 2019-06-10 | Univ Denmark Tech Dtu | Composicion de marcaje palpable. |
| CA3143104A1 (en) | 2019-06-12 | 2020-12-17 | Technical University Of Denmark | Dissacharide formulations for controlled drug release |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853424A (en) * | 1952-08-06 | 1958-09-23 | Schering Ag | X-ray contrast agents comprising symmetrical bifunctional analogs of nu-acyl derivatives of 2, 4, 6 triiodo-3-amino benzoic acid |
| US3178473A (en) * | 1962-03-02 | 1965-04-13 | Nyegaard & Co As | Process for the n-alkylation of acyl anilides halogen substituted in the nucleus |
| US3290366A (en) * | 1963-03-06 | 1966-12-06 | Mallinckrodt Chemical Works | 5-amino-nu-alkyl-2, 4, 6-triiodoisophthalamic acid derivatives |
| GB1033776A (en) * | 1963-06-06 | 1966-06-22 | Sterling Drug Inc | Iodinated acid amides and esters and salts thereof |
| US3732293A (en) * | 1968-03-15 | 1973-05-08 | Sterling Drug Inc | Iodinated bis(aminobenzoic acids) and esters thereof |
| CH502104A (de) * | 1968-05-02 | 1971-01-31 | Bracco Ind Chimica Spa | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
| CH544551A (de) * | 1969-06-27 | 1973-11-30 | Nyegaard & Co As | Neue Röntgenkontrastmittel |
| US3660464A (en) * | 1970-06-19 | 1972-05-02 | Squibb & Sons Inc | Tri-iodinated diaminobenzoic acid derivatives |
| BE787669A (fr) * | 1971-08-17 | 1973-02-19 | Schering Ag | Anilides d'acide n-methyl-dicarboxylique triiodes, et leur procede de preparation |
| DD104193A5 (no) * | 1972-12-22 | 1974-03-05 | ||
| DE2629228C2 (de) * | 1976-06-25 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Jodierte Isophthalamsäure-Derivate Verfahren zu deren Herstellung sowie deren Verwendung |
| CH626873A5 (no) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa |
-
1976
- 1976-06-23 DE DE2628517A patent/DE2628517C2/de not_active Expired
-
1977
- 1977-05-18 NL NLAANVRAGE7705509,A patent/NL189510C/xx not_active IP Right Cessation
- 1977-06-16 FI FI771900A patent/FI67540C/fi not_active IP Right Cessation
- 1977-06-16 DK DK266177A patent/DK150505C/da not_active IP Right Cessation
- 1977-06-20 IE IE1249/77A patent/IE45225B1/en not_active IP Right Cessation
- 1977-06-20 PL PL1977199019A patent/PL108102B1/pl not_active IP Right Cessation
- 1977-06-20 CS CS774059A patent/CS199680B2/cs unknown
- 1977-06-20 GB GB25644/77A patent/GB1588733A/en not_active Expired
- 1977-06-20 GB GB7222/80A patent/GB1588734A/en not_active Expired
- 1977-06-21 CH CH761277A patent/CH629751A5/de not_active IP Right Cessation
- 1977-06-21 GR GR53760A patent/GR71696B/el unknown
- 1977-06-21 LU LU77588A patent/LU77588A1/xx unknown
- 1977-06-21 PT PT66690A patent/PT66690B/pt unknown
- 1977-06-21 IL IL52356A patent/IL52356A/xx unknown
- 1977-06-21 DD DD7700199616A patent/DD131014A5/xx unknown
- 1977-06-22 SU SU772498151A patent/SU917696A3/ru active
- 1977-06-22 SE SE7707230A patent/SE436871B/xx not_active IP Right Cessation
- 1977-06-22 CA CA281,184A patent/CA1106400A/en not_active Expired
- 1977-06-22 HU HU77SCHE611A patent/HU174228B/hu unknown
- 1977-06-22 NO NO772202A patent/NO147447C/no unknown
- 1977-06-22 AU AU26325/77A patent/AU512304B2/en not_active Expired
- 1977-06-22 ES ES460007A patent/ES460007A1/es not_active Expired
- 1977-06-23 BE BE178719A patent/BE856039A/xx not_active IP Right Cessation
- 1977-06-23 ZA ZA00773782A patent/ZA773782B/xx unknown
- 1977-06-23 IT IT7724994A patent/IT1237314B/it active
- 1977-06-23 FR FR7719234A patent/FR2355808A1/fr active Granted
- 1977-06-23 AT AT443777A patent/AT361117B/de not_active IP Right Cessation
- 1977-06-23 JP JP7489777A patent/JPS537637A/ja active Granted
-
1979
- 1979-01-12 US US06/002,901 patent/US4239747A/en not_active Expired - Lifetime
-
1980
- 1980-03-21 CA CA348,166A patent/CA1106401A/en not_active Expired
- 1980-06-18 IL IL60344A patent/IL60344A0/xx unknown
-
1981
- 1981-10-08 IE IE812351A patent/IE45226L/xx not_active IP Right Cessation
-
1982
- 1982-08-04 NO NO822674A patent/NO148811C/no unknown
-
1984
- 1984-12-12 DK DK595284A patent/DK165973C/da not_active IP Right Cessation
-
1985
- 1985-07-09 JP JP60149408A patent/JPS61126059A/ja active Granted
-
1993
- 1993-06-09 LU LU88292C patent/LU88292I2/de unknown
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