9-Hydroxyoctahydrobenzo [C] quinolines and intermediates therefor
Patent 4260764 Issued on April 7, 1981. Estimated Expiration Date: 
May 29, 1999. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
May 29, 1999. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.Patent References 3506654 7-Hydroxy-benzo[ij]quinolizine-2-carboxylic acids, intermediates, and a method for their production 3-Aminomethylene-6,7-dimethoxy-2-methyl-4-ox o-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto Alkyl and benzyl 6,7-dialkoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylates Patent #: 4013662 InventorApplicationNo. 06/042773 filed on 05/29/1979US Classes:546/153, Chalcogen attached directly to the six-membered hetero ring by nonionic bonding544/126, The additional six-membered hetero ring is one of the cyclos in a tricyclo ring system544/361, The additional six-membered hetero ring is one of the cyclos in a polycyclo ring system546/101, Each of the three cyclos is six-membered (e.g., benzoquinolines, etc.)546/108, Phenanthridines (including hydrogenated)546/110, Chalcogen or -C(=X)-, wherein X is chalcogen, attached directly to the six membered hetero ring by nonionic bonding546/15, Spiro546/156, Having -C(=X)-, wherein X is chalcogen, bonded directly to the six-membered hetero ring987/111Contains the structure aryl-(C)n-P where n is at least one (9/54A7)ExaminersPrimary: Daus, Donald G.Assistant: Eakin, M. C. Attorney, Agent or FirmInternational ClassesC07C 37/00 (20060101)C07C 37/055 (20060101) C07D 303/22 (20060101) C07D 303/00 (20060101) C07D 213/30 (20060101) C07D 213/00 (20060101) C07D 215/233 (20060101) C07D 215/00 (20060101) C07D 221/12 (20060101) C07D 221/00 (20060101) C07F 9/00 (20060101) C07F 9/54 (20060101) Abstract1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo[c]quinoline-9(8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof having the formulae ##STR1## wherein R is hydroxy, alkanoyloxy having from one to five carbon atoms and hydroxymethyl;R1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH2)p --NR2 R3 wherein p is 0 or an integer from 1 to 4; each of R2 and R3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R2 and R3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring (piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group); R4 is hydrogen, alkyl having from 1 to 6 carbon atoms and --(CH2)z --C6 H5 wherein z is an integer from 1 to 4; R5 is hydrogen, methyl or ethyl; R6 is hydrogen, --(CH2)y -carbalkoxy having from 1 to 4 carbon atoms in the alkoxy group wherein y is 0 or an integer from 1 to 4; carbobenzyloxy, formyl, alkanoyl having from two to five carbon atoms, alkyl having from one to six carbon atoms; --(CH2)x --C6 H5 wherein x is an integer from 1 to 4; and --CO(CH2)x-1 --C6 H5 ;R0 is oxo, methylene or alkylenedioxy having from two to four carbon atoms;R' is R or R0 ;Z is (a) alkylene having from one to nine carbon atoms; (b)--(alk1)m --X--(alk2)n -- wherein each of (alk1) and (alk2) is alkylene having from one to nine carbon atoms, with the proviso that the summation of carbon atoms in (alk1) plus (alk2) is not greater than 9; each of m and n is 0 or 1; X is 0, S, SO or SO2 ; andW is hydrogen, methyl, ##STR2## wherein W1 is hydrogen, chloro or fluoro, pyridyl, piperidyl, cycloalkyl having from 3 to 7 carbon atoms, or monosubstituted cycloalkyl wherein the substituent is ##STR3## wherein W2 is hydrogen, chloro or fluoro; and pharmaceutically-acceptable acid addition salts of compounds of formulae I, II and IV and the ketals of compounds of formulae II, III and IV wherein the ketal moiety has from two to four carbon atoms.Other References
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