Benzophenone derivatives

Claim 1

251 n The claims defining the invention are as follows. 1. A process for the preparation of benzophenone derivatives of the general formula R. wherein represents a i the group -B-CH-NH2 B represents a methylene or carbonyl group, R 1 represents a hydrogen atom or a lower alkyl group, R2 represents a hydrogen or halogen atom and R3 and R4 each represent a hydrogen atom or a lower alkyl group, which comprises for preparing compounds of the formula N-R 0 RL Ia wherein R1 R 2 and R 3 have the meaning indicated above and R' represents a protecting group, treating a compound of the general formula 26 484,222 71.251 n4 R 0O C=O fII. l II wherein R i R2 R3 and R' have the meaning indicated above, with an oxidizin3 agent, or for preparinL compounds of the formula N-H 0C CO wherein Rl R 2 and R3 have tI e meaning indicated above, of the form- splitting off the protecting group of a compound ula la above, or preparing compounds of the formula R, 0 1o 0 =0 3 Io 484.222 wherein R 1 K* R have the meaning indicated above, R 2 R 3 andliJ.- R- wheei formula reacting a compound of the general Rg 0 4 I II I 00 -o indicated above wherein R, R2R 3 and R' have the meaning alkyl sulfonyloxy or phenyl and Y represents halogen, lower or reacting a compound correspond- sulfonyloxy, with ammonia, which Y represents a carbobenzoxy- ing to formula III, but in acid in the presence of acetic amino group, with a hydrohallc III, corresponding to formula acid, or reacting a compound with hydrazine a phthalimido group, but in which Y relresents reducing a compound corresponding hydrate, or catalytically azido group, or which Y represents an to formula III, but in. the formula for preparing compounds of R^ 1 Id above, R2 P R and R, have the meaning indicated wherein t1 general formula reacting a compound of the 28 484,222 7 1.25 1 n4 R# R wherein Rl, R2 R3 and R4have the meaning indicated above and X represents halogen, with ammonia, or reacting a com- pound corresponding to formula TV, but In which X represents a phthalimido group, with hydrazine hydrate or hydrolyzing a compound corresponding to formula IV, but in which X represents a benzamido group. 2. A process as claimed in Claim 1, wherein Rt Is lower alkanoyl. 3. A process as claimed in Claim 1 or 2 which comprises treating a compound of formula II in Claim 1, wherein R3is hydrogen, with a ceric salt. 4. A process as claimed in Claim 1 or 2 which comprises treating a compound of formula II in Claim I, wherein R3is lower alkyl, with a permanganate Pr with a ceric salt. A process as claimed in Claim 1 or 2, which comprises treating a compound of formula II in Claim 1, with ceric ammonium nitrate, ceric nitrate or cerie sulfate. 6. A process as claimed in Claim 1, wherein R2is' hydrogen or halogen joined at the 2-position of the phenyl ring. 29 4 8 4.2 22. 71.251 n4 7. A process as claimed in Claim 6, wherein R2 is fluorine. 8. A process as claimed in Claim 1, wherein RI is methyl. 9. A process as claimed in Claim 1, wherein R3 is methyl. A process as claimed in Claim 1, 8 or 9, wherein R4 is hydrogen. ii. Benzophenone derivatives of the general formula I* N- R 0 R; .Cri, wherein R represents s hydrogen atom, a protecting grouplor the group -B-CH-NH2 B represents a methylene or carbonyl group, R 1 represents a hydrogen atom or a lower alkyl group, R2 represents a hydrogen or halogen atom and R3 and R4 each represent a hydrogen atom or a lower alkyl group.; 12. Benzophenone derivatives as claimed in Claim 11, wherein R represents a lower alkanpyl group. 13. Benzophenone derivatives as claimed in Claim 11, wherein R represents a hydrogen atom. 14. Benzophenone derivatives as claimed in Claim 12, wherein R 2 represents a hydrogen atom or a halogen atom in the 2'-position. 484.222 71.251 m1 Benzophenone derivatives as claimed in Claim 14, wherein R 2 represents a fluorine atom. 16. Benzophenone derivatives as claimed in Claim 12, 13 or 15, wherein R 1 represents the methyl group. 17. Benzophenone derivatives as claimed in Claim 12, 13 or 15, wherein R represents the methyl group. 18. 2-Acetanido--as~oe enzophenone, according to Claim 11. 19. 5-Acetyl-2-aminobenzophenone, according to Claim 11. 5-Acetyl-2-amino-2' -fluorobenzophenone, according to Claim 11. 21. 2-Acetanido-5-butyrylbenzophenone, according to Claim 11. 22. 2-Amino-5-butyrylbenzophenone, according to Claim 11. 23. Benzophenone derivatives as claimed in Claim 11, wherein R represents the group -B H-NH 2 24. Benzophenone derivatives as claimed in Claim 23, wherein R 4 represents a hydrogen atom. Benzophenone derivatives as claimed in Claim 23, wherein B represents a carbonyl group and R 2 represents a hydrogen atom or a halogen atom in the 2'-position. 26. Benzophenone derivatives as claimed in Claim wherein R 2 represents a fluorine atom. 27. Benzophenone derivatives as claimed in Claim 23, 25 or 26, wherein R 1 represents the methyl group. 31 484.222 7 1.25 1 nl4 as claimed in Claim 28. Benzophenone derivatives group. R represents the methyl 23, 25 or 26, wherein 3 according 29. 5-ctl2gyyaioezpeoe to Claim 11. 2 1-fluorobenzophofloflO 5 -A0etyl-2-gyoylamino- according to Claim-11. according 31. to Claim 11. 19741 DATED this FOURTH day of JULY, H0FFMAdNN-LA ROCHE CO. AKTENGESELLSCHAF'T F. the Applicanlt Patent Attorneys for SPRUSON &FERGUSON 32 4.84.222