US 2014/0275129 A1Published application

Tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone compounds

AssigneeRexahn Pharmaceuticals, Inc.

InventorsYoung Bok Lee, Jae Min Kim, Deog Joong Kim, Chang-Ho Ahn

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Abstract

Tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone derivatives represented by formula (I), pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for treating hyperproliferative disorders by administering the compounds are also described. 1,2,3,4-tetrahydroisoquinoline derivatives for making tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone compounds are also described.

Claims23

Dependent claims

A compound of formula (I):

wherein:
each R1, independently, is hydrogen, halogen, or —O—R4;
R2 is —(CRaRb)z—R5;
each R3, independently, is hydrogen, halogen, —N(R4)2, —O—R4, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each Ra, independently, is hydrogen, halogen, hydroxy, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each Rb, independently, is hydrogen, halogen, hydroxy, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each R4, independently, is hydrogen or C1-C6 alkyl;
R5 is hydrogen, halo, alkyl, hydroxy, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, —N(R4)CO—R4 or Ar;
Ar is aryl or heteroaryl, wherein each of aryl and heteroaryl is optionally substituted by one to five substituents independently selected from hydrogen, halogen, —R4, —N(R4)2, nitro, —(CH2)n—NHCO—R4, —O—R4, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
n is 0, 1, 2, or 3;
x is 0, 1, 2, 3, or 4;
y is 0, 1, 2, 3, or 4;
and
z is 0, 1, 2, 3, 4, 5, or 6;
or a pharmaceutically acceptable salt thereof.

12 more elements

A compound selected from the group consisting of:

2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-fluoro-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methylphenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methylphenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-phenylquinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-phenylquinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-phenylquinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-phenylquinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-phenylquinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methoxylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methoxylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-methoxylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-chlorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-chlorophenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-chlorophenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-chlorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-chlorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(dimethylamino)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(dimethylamino)phenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(dimethylamino)phenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(dimethylamino)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(dimethylamino)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-fluorophenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-fluorophenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-fluorophenyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-methoxylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-methoxylphenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-methoxylphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-methoxylphenyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-(trifluoromethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2,4-difluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2,4-difluorophenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2,4-difluorophenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2,4-difluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2,4-difluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-acetamidophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-acetamidophenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-acetamidophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(acetamidomethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(acetamidomethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(acetamidomethyl)phenyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(acetamidomethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-(acetamidomethyl)phenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-pyrimidinyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-pyrimidinyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-pyrimidinyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-pyrimidinyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2-(acetamido)ethyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2-(acetamido)ethyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2-(acetamido)ethyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2-(acetamido)ethyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(2-(acetamido)ethyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-thiazolyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-thiazolyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-thiazolyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-thiazolyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-thiazolyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-pyridinyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-pyridinyl)quinazolin-4-yl]carbonyl]-5,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-pyridinyl)quinazolin-4-yl]carbonyl]-5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-pyridinyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-dimethylamino-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3-pyridinyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-nitrophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[2-(4-aminophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(4-fluorophenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;
2-[[6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline;
and 2-[[6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-yl]carbonyl]-6-fluoro-1,2,3,4-tetrahydroisoquinoline;
or a pharmaceutically acceptable salt thereof.

118 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/212,031Filed 14 Mar 2014
Priority: 15 Mar 2013
Published: 18 Sep 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

A61K 31/517
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
A61K 47/66
The modifying agent being a protein, peptide or polyamino acid: the modifying agent being a pre-targeting system involving a peptide or protein…
A61P 35/00
Antineoplastic agents
C07D 401/06
Containing two hetero rings: linked by a carbon chain containing only aliphatic carbon atoms

Family

Application61/788,740Us provisional application · filed 15 Mar 2013
US 9,193,707 B2Related patent
US 2014/0275129 A1This patent

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

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Abstract

Facts

Application

14/212,031Filed 14 Mar 2014

Priority

15 Mar 2013

Published

18 Sep 2014

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

A61K 31/517
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
A61K 47/66
The modifying agent being a protein, peptide or polyamino acid: the modifying agent being a pre-targeting system involving a peptide or protein…
A61P 35/00
Antineoplastic agents
C07D 401/06
Containing two hetero rings: linked by a carbon chain containing only aliphatic carbon atoms