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US 5,514,685 AGranted
Heteroatom-containing tricyclic compounds
AssigneeSandoz Ltd.
InventorKarl Baumann
Life of this patent
Estimating the term…
Abstract
The invention concerns the compounds of formulae ##STR1## wherein the substituents have various significances. They can be prepared by various methods, e.g. acylation, reduction, alkylation, etc. They are indicated for use as pharmaceuticals, in particular as immunosuppressant, antiproliferative and antiinflammatory agents.
Claims15
A compound of formulae I to III ##STR11## wherein the symbol .sub.-- -- -- represents a single bond or, when R.sub.2a is absent, a double bond;
- R.sub.1 represents an optionally protected hydroxy group and R.sub.1a represents hydrogen;
- or R.sub.1 and R.sub.1a together represent oxo;
- R.sub.2 represents an optionally protected hydroxy group or together with R.sub.4 forms the --OC(.dbd.O)O-- group, and R.sub.2a represents hydrogen or is absent;
- whereby when the symbol .sub.-- -- -- is a single bond,
- R.sub.2 together with R.sub.2a also represents oxo;
- R.sub.3 represents methyl, ethyl, n-propyl or allyl;
- R.sub.4 represents optionally protected hydroxy or together with R.sub.2 forms the --OC(.dbd.O)O-- group, and R.sub.4a represents hydrogen;
- or R.sub.4 together with R.sub.4a represents oxo;
- R.sub.5 represents alkoxycarbonyloxy, halogen, optionally protected hydroxy, lower alkoxy, acyloxy or a group --OC(.dbd.X)N(R.sub.10)R.sub.11 ;
- or R.sub.5 together with R.sub.6a forms a group --OC(.dbd.X)N(R'.sub.10)-- attached with the nitrogen atom to the carbon atom carrying R.sub.6a, whereby X represents oxygen or sulfur, R.sub.10 and R.sub.11 independently represent hydrogen or lower alkyl or together with the nitrogen atom form a five- or six-membered ring optionally containing a second heteroatom such as nitrogen or oxygen, and R'.sub.10 is hydrogen or lower alkyl;
- or R.sub.5 together with R.sub.8a represents oxy, whereby R.sub.8 represents hydroxy;
- R.sub.6 represents hydroxy, and R.sub.6a represents hydrogen or together with R.sub.5 forms a group --OC(.dbd.X)N(R'.sub.10)-- as defined above;
- or R.sub.6 and R.sub.6a together represent oxo;
- R'.sub.5 represents optionally protected hydroxy, lower alkoxy or acyloxy and
- R'.sub.6 represents hydroxy;
- or R'.sub.5 and R'.sub.6 together form the --OC(.dbd.O)O-- group;
- R".sub.5 represents hydroxy or lower alkoxy and R".sub.6 represents hydroxy;
- or R".sub.5 and R".sub.6 together form the --OC(.dbd.O)O-- group;
- R.sub.7 represents methoxy or hydroxy;
- R.sub.8 represents an optionally protected hydroxy group, acyloxy, imidazolylcarbonyloxy or alkoxycarbonyloxy and R.sub.8a represents hydrogen;
- or R.sub.8 represents hydroxy and R.sub.8a together with R.sub.5 represents oxy;
- or R.sub.8 together with R.sub.8a represents oxo;
- and
- n represents 1 or 2;
- in free form or salt form.
22 more elements
A compound of formulae 1, II, or III ##STR12## wherein the symbol .sub.-- -- -- represents a single bond or, when R.sub.2a is absent a double bond;
- R.sub.1 represents hydroxy or hydroxy protected by tert-butoxycarbonyl, tri(C.sub.1-4)alkylsilyl, or methylsulphonyl and R.sub.1a represents hydrogen;
- or R.sub.1 and R.sub.1 together represent oxo;
- R.sub.2 represents hydroxy or hydroxy protected by tert-butoxycarbonyl, tri(C.sub.1-4)alkylsilyl, or methylsulphonyl or together with R.sub.4 forms the --OC(.dbd.O)O-- group, and
- R.sub.2a represents hydrogen or is absent;
- and when the symbol .sub.-- -- -- is a single bond,
- R.sub.2 together with R.sub.2a also represents oxo;
- R.sub.3 represents methyl, ethyl, n-propyl or allyl;
- R.sub.4 represents hydroxy or hydroxy protected by tert-butoxycarbonyl, tri(C.sub.1-4)alkylsilyl, or methylsulphonyl or together with R.sub.2 forms the --OC(.dbd.O)O-- group, and R.sub.4a represents hydrogen;
- or
- R.sub.4 together with R.sub.4a represents oxo;
- R.sub.5 represents (C.sub.1-4)alkoxycarbonyloxy, halogen, hydroxy or hydroxy protected by tri (C.sub.1-4) alkylsilyl or methylsulphonyl, (C.sub.1-4)alkoxy, (C.sub.1-4)alkylcarbonyloxy, formyloxy, benzyloxy or a group --OC(.dbd.X)N(R.sub.10)R.sub.11 ;
- or R.sub.5 together with R.sub.6a forms a group --OC(.dbd.X)N(R'.sub.10)-- attached with the nitrogen atom to the carbon atom carrying R.sub.6a' wherein X represents oxygen or sulfur R.sub.10 and R.sub.11 independently represent hydrogen or (C.sub.1-4)alkyl or together with the nitrogen atom form 4-morpholinyl;
- R'10 represents hydrogen or (C.sub.1-4)alkyl;
- or
- R.sub.5 together with R.sub.8a represents oxy and R.sub.8 represents hydroxy;
- R.sub.6 represents hydroxy, and
- R.sub.6a represents hydrogen or together with R.sub.5 forms a group --OC(.dbd.X)N(R'.sub.10)-- as defined above;
- or
- R.sub.6 and R.sub.6a together represent oxo;
- R'.sub.5 represents hydroxy or hydroxy protected by tert-butoxycarbonyl, tri(C.sub.1-4)alkylsilyl, or methylsulphonyl, (C.sub.1-4)alkoxy or (C.sub.1-4)alkylcarbonyloxy, formyloxy, benzyloxy and
- R'.sub.6 represents hydroxy;
- or
- R'.sub.5 and R'.sub.6 together form the --OC(.dbd.O)O-- group;
- R".sub.5 represents hydroxy or (C.sub.1-4) alkoxy and R".sub.6 represents hydroxy;
- or
- R".sub.5 and R".sub.6 together form the --OC(.dbd.O)O-- group;
- R.sub.7 represents methoxy or hydroxy;
- R.sub.8 represents hydroxy or hydroxy protected by tri (C.sub.1-4) alkylsilyl or methylsulphonyl, (C.sub.1-4)alkylcarbonyloxy, formyloxy, benzyloxy, imidazolylcarbonyloxy or (C.sub.1-4) alkoxycarbonyloxy and
- R.sub.8a represents hydrogen;
- or
- R.sub.8 represents hydroxy and R.sub.8a together with R.sub.5 represents oxy;
- or
- R.sub.8 together with R.sub.8a represents oxo;
- and
- n represents 1 or 2;
- in free form.
33 more elements
Dependencies are inferred from the claim text.