Valency platform molecules comprising carbamate linkages

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

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Details

C560S026000, C560S115000, C560S158000, C530S402000, C530S409000

Reexamination Certificate

active

06458953

ABSTRACT:

TECHNICAL FIELD
This invention pertains generally to valency molecules. The invention also relates to the field of valency platform molecules which act as scaffolds to which one or more molecules may be covalently tethered to form a conjugate. More particularly, the present invention pertains to valency molecules which comprise a carbamate linkage (i.e., —O—C(═O)—N<). In one aspect, the present invention pertains to valency platforms comprising carbamate linkages, which molecules have the structure of any one of Formulae I, II, or III, shown in FIG.
1
. In one aspect, the present invention pertains to valency platforms comprising carbamate linkages, which molecules have the structure of any one of Formulae IV, V, or VI, shown in FIG.
8
. The present invention also pertains to methods of preparing such valency molecules, conjugates comprising such valency molecules, and methods of preparing such conjugates.
BACKGROUND
A “valency platform” is a molecule with one or more (and typically multiple) attachment sites which can be used to covalently attach biologically active molecules of interest to a common scaffold. The attachment of biologically active molecules to a common scaffold provides multivalent conjugates in which multiple copies of the biologically active molecule are covalently linked to the same platform. A “defined” or “chemically defined” valency platform is a platform with defined structure, thus a defined number of attachment points and a defined valency. A defined valency platform conjugate is a conjugate with defined structure and has a defined number of attached biologically active compounds. Examples of biologically active molecules include oligonucleotides, peptides, polypeptides, proteins, antibodies, saccharides, polysaccharides, epitopes, mimotopes, drugs, and the like. In general, biologically active compounds interact specifically with proteinaceous receptors.
Certain classes of chemically defined valency platforms, methods for their preparation, conjugates comprising them, and methods for the preparation of such conjugates, have been described in the U.S. Pat. Nos. 5,162,515; 5,391,785; 5,276,013; 5,786,512; 5,726,329; 5,268,454; 5,552,391; 5,606,047; and 5,663,395.
The valency platforms of the present invention reflect a new class of valency platforms which comprise a carbamate linkage, as shown, for example, in Formulae I, II, and III in FIG.
1
and in Formulae IV, V, and VI in FIG.
8
.
SUMMARY OF THE INVENTION
One aspect of the present invention pertains to a valency platform compound having the structure of one of the following formulae:
wherein:
n is a positive integer from 1 to 10;
y
1
, y
2
, and y
3
are independently 1 or 2;
J independently denotes either an oxygen atom or a covalent bond;
R
C
is selected from the group consisting of:
hydrocarbyl groups having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, nitrogen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, sulfur, and hydrogen atoms, and having from 1 to 20 carbon atoms;
each G
1
, G
2
, and G
3
is independently selected from the group consisting of:
hydrocarbyl groups having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, nitrogen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
each R
N
is independently selected from the group consisting of: hydrogen;
linear or branched alkyl groups having from 1 to 15 carbon atoms;
alkyl groups comprising an alicyclic structure and having from 1 to 15 carbon atoms;
aromatic groups having from 6 to 20 carbon atoms;
heteroaromatic groups having from 3 to 20 carbon atoms;
each Z is independently selected from the group consisting of:
—H
—C(═O)OR
CARB
—C(═O)R
ESTER
—C(═O)NR
A
R
B
wherein:
each R
CARB
is organic groups comprising from 1 to about 20 carbon atoms;
each R
ESTER
is organic groups comprising from 1 to about 20 carbon atoms;
each group —NR
A
R
B
is independently selected from the group consisting of:
—NH
2
—NHR
A
—NR
A
R
B
—NR
AB
wherein each monovalent R
A
and R
B
and each divalent R
AB
is independently an organic group comprising from 1 to 20 carbon atoms, and further comprising a reactive conjugating functional group.
In one embodiment, said compound has the structure of Formula I. In one embodiment, said compound has the structure of Formula II. In one embodiment, said compound has the structure of Formula III. In one embodiment, said compound has the structure of Formula IV. In one embodiment, n is a positive integer from 2 to 4. In one embodiment, y
1
, y
2
, and y
3
are each 2. In one embodiment, J is an oxygen atom. In one embodiment, J is a covalent bond. In one embodiment, R
C
is selected from the group consisting of hydrocarbyl groups having from 1 to 20 carbon atoms. In one embodiment, R
C
is selected from the group consisting of:
In one embodiment, R
C
is selected from the group consisting of organic groups consisting only of carbon, oxygen, and hydrogen atoms, and having from 1 to 20 carbon atoms. In one embodiment, R
C
is:
wherein p is a positive integer from 2 to 20. In one embodiment, each G
1
, G
2
, and G
3
is independently selected from the group consisting of hydrocarbyl groups having from 1 to 20 carbon atoms. In one embodiment, each G
1
, G
2
, and G
3
is —(CH
2
)
q
— wherein q is a positive integer from 1 to 20. In one embodiment, each G
1
, G
2
, and G
3
is independently selected from the group consisting of organic groups consisting only of carbon, oxygen, and hydrogen atoms, and having from 1 to 20 carbon atoms. In one embodiment, each G
1
, G
2
, and G
3
is:
wherein p is a positive integer from 2 to 20. In one embodiment, R
N
is independently selected from the group consisting of —H, —CH
3
, and —CH
2
CH
3
. In one embodiment, each group —NR
A
R
B
is independently selected from the group consisting of:
Another aspect of the present invention pertains to a valency platform compound having the structure of one of the following formulae:
wherein:
n is a positive integer from 1 to 10;
y
1
, y
2
, and y
3
are independently a positive integer from 1 to 10;
J independently denotes either an oxygen atom or a covalent bond;
R
C
is selected from the group consisting of:
hydrocarbyl groups having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, nitrogen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, sulfur, and hydrogen atoms, and having from 1 to 20 carbon atoms;
each G
1
, G
2
, and G
3
is independently selected from the group consisting of:
hydrocarbyl groups having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
organic groups consisting only of carbon, oxygen, nitrogen, and hydrogen atoms, and having from 1 to 20 carbon atoms;
each R
N
is independently selected from the group consisting of:
hydrogen;
linear or branched alkyl groups having from 1 to 15 carbon atoms;
alkyl groups comprising an alicyclic structure and having from 1 to 15 carbon atoms;
aromatic groups having from 6 to 20 carbon atoms;
heteroaromatic groups having from 3 to 20 carbon atoms;
each Z is independently selected from the group consisting of:
—H
—C(═O)OR
CARB
—C(═O)R
ESTER
—C(═O)NR
A
R
B
wherein:
each R
CARB
is organic groups comprising from 1 to about 20 carbon atoms;
each R
ESTER
is organic groups comprising from 1 to about 20 carbon atoms;
each group —NR
A
R
B
is independently selected from the group consisting of:
—NH
2
—NHR
A
—NR
A
R
B
—NR
AB
wherein each monovalent R
A
and R
B
and each divalent R
AB
is independently an organic group compri

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