US 5,516,931 A · Release tag compounds producing ketone signal groups

Abstract

A release tag reagent suitable for use in the chemical analysis of a substance to be detected comprises signal, release, and reactivity groups. A class of release tag compounds that are cleaved to release as signal groups very stable electrophoric ketones which are sufficiently volatile for determination in the gas phase of an analytical reaction mixture is disclosed.

Claims13

Dependent claims

A ketone compound having the structure ##STR26## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 =D, or F (m=1 to 4);
R, OR, NR.sub.2 (m=1 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
Z=o-phenylene or propylene as part of a five- or six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl, or phenyl which can contain one or more of H, D, or F;
Q=--CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
and
Ar=phenylene or phenylenoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring.

6 more elements

An olefin release tag compound having the structure ##STR27## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 =H, D, or F (m=0 to 4);
R, OR, NR.sub.2 (m=0 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
R.sup.5 =H or R;
Z=o-phenylene or propylene as part of a six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl or phenyl which can contain one or more of H, D, or F;
Q=-CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
Ar=phenylene or phenyleneoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring;
and
Rx=reactivity group.

8 more elements

A glycol release tag compound having the structure ##STR28## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 H, D, or F (m=0 to 4);
R, OR, NR.sub.2 (m=0 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
R.sup.5 =H or R;
Z=o-phenylene or propylene as part of a six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl or phenyl which can contain one or more of H, D, or F;
Q=--CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
Ar=phenylene or phenyleneoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring;
and
Rx=reactivity group.

8 more elements

An .alpha.-hydroxyketo release tag compound having the structure ##STR29## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 =H, D, or F (m=0 to 4);
R, OR, NR.sub.2 (m=0 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
Z=o-phenylene or propylene as part of a six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl or phenyl which can contain one or more of H, D, or F;
Q=--CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
Ar=phenylene or phenyleneoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring;
and
CORx'=reactivity group.

7 more elements

Dependencies are inferred from the claim text.

Facts

Application

08/053,608Filed 22 Apr 1993 · continuation in part

Priority

1 Feb 1982

Granted

14 May 1996

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

G01N 33/582
Involving labelled substances: with fluorescent label
C07D 207/46
Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom: with…
G01N 33/532
Production of immunochemical test materials: production of labelled immunochemicals
G01N 33/78
Involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and…:…

Family

Serial344,394Parent of this continuation-in-part · filed 1 Feb 1982

Serial710,318Parent of this continuation-in-part · filed 11 Mar 1985

US 5,360,819 AParent of this continuation-in-part

US 4,709,016 AParent of this continuation-in-part

US 5,516,931 AThis patent

From the US filing history. Foreign family members aren’t listed.

Abstract

Claims13

Dependent claims

A ketone compound having the structure ##STR26## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 =D, or F (m=1 to 4);
R, OR, NR.sub.2 (m=1 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
Z=o-phenylene or propylene as part of a five- or six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl, or phenyl which can contain one or more of H, D, or F;
Q=--CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
and
Ar=phenylene or phenylenoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring.

6 more elements

An olefin release tag compound having the structure ##STR27## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 =H, D, or F (m=0 to 4);
R, OR, NR.sub.2 (m=0 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
R.sup.5 =H or R;
Z=o-phenylene or propylene as part of a six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl or phenyl which can contain one or more of H, D, or F;
Q=-CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
Ar=phenylene or phenyleneoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring;
and
Rx=reactivity group.

8 more elements

A glycol release tag compound having the structure ##STR28## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 H, D, or F (m=0 to 4);
R, OR, NR.sub.2 (m=0 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
R.sup.5 =H or R;
Z=o-phenylene or propylene as part of a six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl or phenyl which can contain one or more of H, D, or F;
Q=--CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
Ar=phenylene or phenyleneoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring;
and
Rx=reactivity group.

8 more elements

An .alpha.-hydroxyketo release tag compound having the structure ##STR29## wherein R.sup.1 =H, CF.sub.3, R, or OR (n=0 to 2);

R.sup.2 =H, D, or F (m=0 to 4);
R, OR, NR.sub.2 (m=0 to 2);
or R.sup.2 plus R.sup.3 =Z;
R.sup.3 =R, or R.sup.2 plus R.sup.3 =Z;
Z=o-phenylene or propylene as part of a six-membered ring which can contain one or more of H, D, F, or R;
R=C1 to C8 alkyl, benzyl or phenyl which can contain one or more of H, D, or F;
Q=--CH.sub.2 O--, --CH.sub.2 N(COR)--, --CONH--, --CONR--, --CON(COR)--, --CH.sub.2 OAr--, or --CONHAr--;
Ar=phenylene or phenyleneoxy or benzyleneoxy which can contain one or more of H, D, F or R on the aromatic ring;
and
CORx'=reactivity group.

7 more elements

Dependencies are inferred from the claim text.

Release tag compounds producing ketone signal groups

Life of this patent

Abstract

Claims13

Release tag compounds producing ketone signal groups

Life of this patent

Abstract

Claims13