Claims
- 1. A process for the production of a compound of the following Formula I ##STR13## wherein A is N or CR.sub.2 ;
- B is N or CR.sub.2 ;
- D is N or CR.sub.3 ;
- R is hydrogen, hydroxy, loweralkyl, loweralkoxy, cycloalkyl, aryl, aryloxy, pyridinyl, 3-pyridinyloxy, R.sub.6 S(O).sub.n, W--ALK--Q, --N(R.sub.7).sub.2, ##STR14## R.sub.1 is hydrogen, hydroxy, loweralkyl, loweralkoxy, cycloalkyl, aryl, aryloxy, pyridinyl, 3-pyridinyloxy, R.sub.6 S(O).sub.n, W--ALK--Q, --N(R.sub.7).sub.2, ##STR15## R.sub.2 is hydrogen, C.sub.1 -C.sub.8 straight or branched chain alkyl optionally substituted by 2 adjacent hydroxyl groups, C.sub.3 -C.sub.8 straight or branched chain alkenyl, loweralkylloweralkoxy, aryl, pyridinyl, loweralkylcycloalkyl, loweralkylaryl, loweralkylpyridinyl, loweralkylaryloxy, loweralkylpyridinyloxy, loweralkyl-N(R.sub.8).sub.2, ##STR16## R.sub.3 is hydrogen, loweralkyl, aryl, pyridinyl, loweralkylaryloxy or loweralkylpyridinyl;
- R.sub.4 is hydrogen, C.sub.1 -C.sub.8 straight or branched chain alkyl, C.sub.3 -C.sub.8 straight or branched chain alkenyl, loweralkylcycloalkyl or loweralkylaryl;
- R.sub.5, R.sub.5 ' are the same or independently hydrogen or loweralkyl;
- R.sub.6 is loweralkyl, aryl, pyridinyl, loweralkylaryl or loweralkylpyridinyl;
- R.sub.7 are the same or independently hydrogen, loweralkyl, aryl or pyridinyl;
- R.sub.8 is the same as R.sub.7 ;
- Q is ##STR17## W is hydrogen, hydroxy, loweralkyl, loweralkoxy, aryl, aryloxy, pyridinyl which may be substituted by 1 or 2 hydroxy groups, pyridinyloxy, ##STR18## R.sub.9, R.sub.10 take the same meaning as R.sub.7 ; R.sub.11 are the same or independently hydrogen or methyl;
- X is --CH.sub.2 --, --O--, --S(O).sub.n -- or --NR.sub.10 ;
- ALK is a C.sub.1 -C.sub.4 straight or branched chain alkyl optionally substituted by a mono hydroxyl group which cannot be attached to a carbon atom adjacent to Q or W when Q or W are hetero atoms;
- n is the integer 0, 1 or 2;
- p is the integer 0 or 1;
- and the pharmaceutically acceptable salts thereof;
- with the proviso that:
- only one of A and B and
- only one of B and D can be N
- which comprises reacting a compound of the following Formula II: ##STR19## wherein R, R.sub.1, A, B and D have the same meaning as in Formula I; with a 1-4 equivalent excess of a doubly activated carbonic acid derivative in an inert aprotic solvent at a temperature of from 150.degree. C. to about 200.degree. C. for about 30 minutes to 6 hours.
- 2. A process of claim 1, wherein said doubly activated carbonic acid derivative is carbonyldiimidazole, said inert aprotic solvent is 1,2-dichlorobenzene, said temperature range is about 150.degree.-180.degree. C. and said duration of the reaction about 1 h.
- 3. A process of claim 1 wherein B is N, A is CR.sub.2 and D is CR.sub.3.
- 4. A process of claim 1 wherein D is N, A is CR.sub.2 and B is CR.sub.2.
- 5. A process of claim 4, the product of which is 9-ethyl-4-[N-2-(pyridin-2-yl)ethyl)-methylamino]imidazo[5,1-H]-pteridin-6(5H)-one, 9-ethyl-4-[(1-methylpiperidin-4-yl)methylamino]imidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-4-[N-(phenylmethyl)methylamino]imidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-4-(methylamino)imidazo-[5,1-h]pteridin-6(5H)-one, 9-ethyl-7-methyl-4-[N(2-dimethylamino)ethyl)methylamino]imidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-4-[(1-methylpiperidin-4-yl)amino]imidazo[5,1-h)pteridin-6(5H)-one, 9-ethyl-4-[(2-hydroxyethyl)methylamino]imidazo[5,1-H]pteridin-6(5H)-one, 9-ethyl-2-(2-ethyl-4-methyl-1H-imidazol-1-yl)-4,7-dimethylimidazo[5,1-h]pteridin-6-(5H)-one, 9-ethyl-4-[(2-hydroxyethyl)amino]-7-methylimidazo[5,1-h]pteridin-6-(5H)-one, 4,9-diethyl-2-(2-ethyl-4-methyl-1H-imidazol-1-yl)-7-methylimidazo[5,1-h]-teridin-6(5H)-one, 9-ethyl-2-(2-ethyl-4-methyl-1H-imidazol-1-yl)-7-methyl-4-(2-propyl)imidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-2-(methylsulfonyl)-4-[(N-phenylmethyl)methylamino]imidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-2-[[(2-diethylamino)ethyl]amino]-4-[(N-phenylmethyl)methylamino]imidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-2-[(2-diethylamino)ethyl]-amino-4-methylaminoimidazo[5,1-h]pteridin-6(5H)-one, 4-(dimethylamino)-9-((morpholin-4-yl)methyl)imidazo[5,1-h]pteridino-6(5H)-one, 9-ethyl-7-methyl-4(dimethylamino)-imidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-7-methyl-4-(dimethylamino)-2-methylthioimidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-7-methyl-4-(dimethylamino)-2-(methylsulfonyl)imidazo[5,1-h]pteridin-6(5H)-one, 4,9-diethyl- 2-(2-ethyl-1H-imidazol-1-yl)imidazo[5,1-h]pteridin-6(5H)-one, 4,9-diethyl-2-(1H-imidazol-1-yl)-imidazo[5,1-h]pteridin-65(H)-one, 9-ethyl-2-(2-ethyl-1H-imidazol-1-l)-4-propylimidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-2-(1H-imidazol-1-yl)-4-propylimidazo[5,1-h]pteridin-6(5H)-one, 9-ethyl-4-(2-(diethylamino)ethyl)-amino-7-methylimidazo[5,1-h]pteridin-6(5H)-one or 4,7-dimethyl-9-ethyl-2-(methylsulfonyl)imidazo[5,1-h]pteridin-6(5H)-one.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a division of U.S. Ser. No. 07/961,987, filed Oct. 16, 1992; which is a continuation-in-part of U.S. Ser. No. 07/844,324 filed Mar. 2, 1992, now abandoned; which is a continuation of U.S. Ser. No. 649,384, filed Feb. 1, 1991, now abandoned; which is a continuation-in-part of U.S. Ser. No. 437,574 filed Nov. 17, 1989, now abandoned, whose disclosures are incorporated herein by reference.
US Referenced Citations (8)
Foreign Referenced Citations (3)
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400583 |
Dec 1990 |
EPX |
429149 |
May 1991 |
EPX |
2106109 |
Apr 1983 |
GBX |
Non-Patent Literature Citations (4)
Entry |
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Divisions (1)
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961987 |
Oct 1992 |
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Continuations (1)
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649384 |
Feb 1991 |
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Continuation in Parts (2)
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844324 |
Mar 1992 |
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437574 |
Nov 1989 |
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