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Details for Patent: 4,980,502

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Details for Patent: 4,980,502

Title: Paramagnetic chelates
Abstract:Compounds suitable for NMR imaging having the formula: ##STR1## wherein a is 2 or 3; b is an integer from 0 to 4; Me.sup.(a+) is Fe.sup.(2+), Fe.sup.(3+), Gd.sup.(3+), or Mn.sup.(2+) ; E.sup.(b+) is an ion of an alkali metal, alkaline earth metal, alkyl ammonium, alkanol ammonium, polyhydroxyalkyl ammonium, or basic protonated amino acid, said ions representing a total charge of b; m is an integer from 1 to 5; R is H, alkyl with from 1 to 8 carbon atoms, alkyl with from 1 to 8 carbon atoms wherein from 1 to 5 carbons are substituted with OH; aralkyl with 1 to 4 aliphatic carbon atoms; phenyl or phenyl substituted by halogen, hydroxyl, carboxyl, carboxamide, ester, SO.sub.3 H, sulfonamide, lower alkyl, lower hydroxy alkyl, amino, acylamino; (poly)oxa-alkyl with 1 to 50 oxygen atoms and from 3 to 150 carbon atoms, wherein 1 to 5 hydrogen atoms may be substituted by OH; R.sub.1 is the same as R.sub.2 or is --CH.sub.2 COOZ, --CH(CH.sub.3)COOZ, CH.sub.2 CH.sub.2 --N(CH.sub.2 COOZ).sub.2, a hydroxy arylalkyl, hydroxy pyridylalkyl, hydroxy aryl(carboxy)alkyl or hydroxy pyridyl-(carboxyl)-alkyl radical, where the aryl or pyridyl radical may be substituted by hydroxyl, hydroxy alkyl, alkyl, halogen, carboxyl or SO.sub.3 H; is --CH.sub.2 COOZ, --CH(CH.sub.3)COOZ, ##STR2## wherein R.sub.3 is --CH.sub.2 COOZ, --CH(CH.sub.3)COOZ or a monovalent radical having the structure ##STR3## X is a direct chemical bond, --O--, --S--, 13 NH--, n is the integer 2 or 3, with the proviso that when X represents a direct bond, n is 1, 2 or 3; Z is hydrogen or a unit of negative charge, and --(CH.sub.2).sub.m -- may also be --CH.sub.2 --C(CH.sub.3).sub.2 --.
Inventor(s): Felder; Ernst (Riva S Vitale, CH), Uggeri; Fulvio (Codogno, IT), Fumagalli; Luciano (Milan, IT), Vittadini; Giorio (Milan, IT)
Assignee: Bracco Industria Chimica, S.p.A. (Milan, IT)
Filing Date:Sep 25, 1989
Application Number:07/411,906
Claims:1. A compound having the formula ##STR62## wherein: is the group --A--O--R wherein;

A is --(CH).sub.2).sub.m --; --CH.sub.2 --C--(CH.sub.3).sub.2 --;

m is an integer from 1 to 5;

R is H; linear or branched alkyl of 1 to 8 carbon atoms, said carbon atoms being unsubstituted or substituted by one or more hydroxy group; aralkyl of 1 to 4 aliphatic carbon atoms; phenyl or phenyl substituted by halogen, amino or hydroxy; (poly)-oxa-alkyl of 1 to 10 oxygen atoms and from 3 to 30 carbon atoms;

R.sub.1 is --CH.sub.2 COOZ; --CH(CH.sub.3)COOZ; --(CH.sub.2).sub.n --N(CH.sub.2 COOZ).sub.2 ; hydroxy-arylalkyl radical, in which the aryl radical is unsubstituted or substituted by hydroxy;

R.sub.2 is --CH.sub.2 COOZ; --CH(CH.sub.3)COOZ; ##STR63## wherein R.sub.3 is --CH.sub.2 COOZ; --CH(CH.sub.3)COOZ; a monovalent radical having the structure ##STR64## X is a direct chemical bond; --O--; --S--; --NH--; ##STR65## n is the integer 2 or 3, with the proviso that when X is a direct chemical bond, n is 1, 2 or 3;

Z is H or a negative charge.

2. A substituted .alpha.-amino propionic acid of formula ##STR66## wherein: is:

(1) --CH.sub.2 OR.sub.5 ;

(2) --C(CH.sub.3).sub.2 --CH.sub.2 OR.sub.5 ;

wherein R.sub.5 is

(a) phenyl;

(b) benzyl;

(c) 1-8 carbon alkyl;

(d) dihydroxy substituted lower alkyl;

(e) --H;

(f) --(OCH.sub.2 --CH.sub.2).sub.p CH.sub.3

wherein p is an integer number between 1 and 5;

and R.sub.4 is --(CH.sub.2).sub.n --X--(CH.sub.2).sub.n --N(CH.sub.2 COOZ).sub.2

wherein X is:

(a) a direct chemical bond;

(b) --O--; ##STR67## and n is 1, 2 or 3 when X is a direct bond or the integer is 2 or 3 and Z is H or a negative charge.

3. A substituted .alpha.-amino propionic acid of formula ##STR68## wherein is --CH.sub.2 --OR.sub.5 wherein R.sub.5 is: (a) benzyl;

(b) --CH.sub.2 --CH.sub.2 --phenyl;

(c) lower alkyl of 1-3 carbon atoms;

(d) H;

and R.sub.4 is ##STR69## wherein Y is: (1) benzyl;

(2) --CH.sub.2 --CH.sub.2 --phenyl:

(3) lower alkyl of 1 to 3 carbon atoms;

(4) H

X is

(a) a direct chemical bond;

(b) --O--; ##STR70## n is 1 when X is a direct chemical bond or 2 when X is (b) or (c); Z is H or a negative charge.

4. A substituted .alpha.-amino propionic acid of formula ##STR71## wherein: is --CH.sub.2 --O--R.sub.5 ; --C(CH.sub.3).sub.2 --CH.sub.2 --O--R.sub.5 ; wherein R.sub.5 is

(a) H;

(b) lower alkyl of 1 to 3 carbon atoms;

(c) dihydroxy substituted lower alkyl;

(d) (CH.sub.2 CH.sub.2 O).sub.1-5 CH.sub.3 ; ##STR72## wherein Y is (a) H;

(b) lower alkyl (1-3 carbon atoms);

(c) dihydroxysubstituted lower alkyl;

(d) (CH.sub.2 CH.sub.0 O).sub.1-5 CH.sub.3 ;

X is

(a) a direct chemical bond;

(b) --O--; ##STR73## n is 1 when X is (a) or 2 when X is (b) or (c); and Z is H or a negative charge.

5. A substituted .alpha.-amino propionic acid of formula ##STR74## wherein: is --CH.sub.2 --O--R.sub.5 ; --C(CH.sub.3).sub.2 --CH.sub.2 --O--R.sub.5 ;

wherein R.sub.5 is

(a) lower alkoxy of 1 to 3 carbon atoms;

(b) benzyl;

(c) (CH.sub.2 CH.sub.2 O).sub.1-5 CH.sub.3 ;

n is the integer 1 or 2;

Z is H or a negative change.

6. The compound according to claim 1 wherein ##STR75## is selected from the group consisting of 3-hydroxy-2-N[2'-N'-[2"-N",N"-bis-(carboxymethyl)-aminoethyl]-N'-(carboxym ethyl)-aminoethyl]-N-(carboxymethyl)-amino-propionic acid

3-phenylmethoxy-2-N-[2'N'-[2"-N",N"-bis-(carboxymethyl)-aminoethyl[-N'-(car boxymethyl)-aminoethyl]-N-(carboxymethyl)-aminopropionic acid,

3-methoxy-b 2-N,N-bis-[2'-N,N'-bis-(carboxymethyl)-aminoethyl]aminopropionic acid,

3-phenylmethoxy-b 2-N,N-bis-[2'-N',N'-bis(carboxymethyl)-aminoethyl]aminopropionic acid,

4-(3,6,9,12,15-pentaoxahexadecyloxy)-3,3-dimethyl-b 2-N[2'-N'-[2"-N",N"-bis-(carboxymethyl)-aminoethyl]-N,-carboxymethyl)-amin oethyl-N-(carboxymethyl)-amino-butric acid,

4-(3,6,9,12,15-pentaoxahexadecyloxy)-3,3-dimethyl-b 2-N, N-bis-[2'-N,,N'-bis-(carboxymethyl)-aminoethyl]-amino-butryic acid,

3-hydroxy-b 2-N-[2'-N',N'-bis-(carboxymethyl)-aminoethyl]-N-(carboxymethyl)-amino-prop ionic acid,

3-phenylmethoxy-b 2-N-[2'-N',N'-bis-(carboxymethyl)-aminoethyl]-N-(carboxymethyl)-amino-prop ionic acid,

3-octyloxy-b 2-N-[2'-N',N'-bis-(carboxymethyl)-aminoethyl]-N-(carboxymethyl)-amino-prop ionic acid,

N,N'-bis-(2-hydroxy-1-carboxy-1-ethyl)-N,N'-bis-(carboxymethyl)ethylene diamine,

4-methoxy-3,3-dimethyl-b 2-N-[2'-N',N'-bis-(carboxymethyl)-aminoethyl]-N-(carboxymethyl)-amino-buty ric acid,

3-phenylmethoxy-b 2-N-[2-[2-N',N'-bis-(carboxymethyl)-aminoethyoxy]ethyl]-N-(carboxymethyl)a minopropionic acid,

N,N'-bis-(2-methoxy-1-carboxyl-1-ethyl)-N,N'-bis-(2-hydroxy phenylmethyl)-ethylene diamine,

N,N'-bis-(3,6,9,12-tetraoxa-1-carboxy-1-tridecyl)-N,N'-bis-(2-hydroxy-pheny lmethyl)-ethylene diamine,

N,N'-bis-(3-methoxy-2,2-dimethyl-1-carboxy-1-propyl-N,N-bis-(2-hydroxy-phen ylmethyl)-ethylene diamine,

N,N'-bis-3-(2,3-dihydroxypropoxhy)-2,2-dimethyl-1-carboxy-1-propyl)-N,N'-bi s-(2-hydroxy-phenylmethyl)-ethylene diamine.
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