http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CA-1310009-C
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_72e761193f0c3c4cb144987d9839c456 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J17-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J41-005 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J51-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-0053 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J21-005 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J21-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J17-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J51-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J41-00 |
| filingDate | 1985-03-13-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| grantDate | 1992-11-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_4e9ec2f60f306ccd6b0e5b0a91459d38 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_1fdd804d26b75015b2ec84ae377d3714 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_1256b0f11a116723c39aba1a4834416f http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0a5b3f8c538461419a39b5a1a3d58fb9 |
| publicationDate | 1992-11-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | CA-1310009-C |
| titleOfInvention | Ester prodrugs of steroids |
| abstract | ABSTRACT ESTER PRODRUGS OF STEROIDS A compound of the formula wherein the dotted line between positions C-1 and C-2 means the presence or absence of a double bond; wherein R1 is CH3 or -C2H5; wherein R2 is H, and R3 is in the .alpha.-position and is -OH, -O-alkyl(C1-C12), -O?alkyl(C1-C12), =O?aryl, -C?N(R)2, or -O?OR7 wherein aryl is furyl, thienyl, pyrrolyl, or pyridyl wherein each of said hetero moiety is optionally substituted with one or two (C1-C4)-alkyl groups or aryl is -(CH2)f-phenyl wherein f is 0 to 2 and wherein the phenyl ring is optionally substituted with 1 to 3 groups selected from chlorine, fluorine, bromine, alkyl(C1-C3), alkoxy(C1-C3), thio-alkoxy(C1-C3), Cl3C-, F3C-, -NH2 and -NHCOCH3 and wherein R is hydro-gen, alkyl(C1-C4), or phenyl and each R can be the same or different; and wherein R7 is aryl as herein defined or alkyl(C1-Cl2); or wherein R2 is .alpha.-Cl and R3 is .beta.-Cl; or wherein R2 and R3 taken together are oxygen (-O-) bridging positions C-9 and C-11; or wherein R2 and R3 taken together form a double bond between positions C-9 and C-11. wherein R4 is H, CH3, Cl or F; wherein R5 is H, OH, F, Cl, Br, CH3, phenyl, vinyl or allyl; wherein R6 is H or CH3; wherein R9 is H, OH, CH3, F or =CH2; wherein R10 is H, OH, CH3 or R10 forms a second bond between positions C-16 and C-17; wherein R11 is -CH2CH2COOH, -Y-(CH2)n-X-(CH2)m-SO3H, -Y'-(CH2)p-X'-(CH2)q-NR12R13 or -Z(CH2)rQ, wherein Y is a bond or -O-; Y' is a bond, -O-, or -S-; each of X and X' is a bond, -CON(R14)-, -N(R14)CO-, -O-, -S-, -S(O)-, or -S(O2)-; R14 is hydrogen or alkyl(C1-C4); each of R12 and R13 is a lower alkyl group of from 1 to 4 carbon atoms optionally substituted with one hydroxyl or R12 and R13 taken together with the nitrogen atom to which each is attached forms a monocyclic hetero-cyclic selected from pyrrolidino, piperidino, morpholino, thiomorpho-lino, piperazino or N(lower)alkylpiperazino wherein alkyl has from 1 to 4 carbon atoms; n is an integer of from 4 to 9; m is an integer of from 1 to 5; p is an integer of from 2 to 9; q is an integer of from 1 to 5; Z is a bond or -O-; r is an integer of from 2 to 9; and Q is (1) -R15-CH2COOH wherein R15 is -S-, -S(O)-, -S(O)2-, -SO2N-(R16)-, or -N(R16)SO2-; and R16 is hydrogen or lower alkyl(C1-C4); with the proviso that the total number of carbon atoms in R16 and (CH2)r is not greater than 10; (2) -CO-COOH; or (3) -CON(R17)CH(R18)COOH wherein R17 is H and R18 is H, CH3, CH2COOH, -CH2CH2COOH, -CH2OH, -CH2SH, -CH2CH2SCH3, or -N(R17)-wherein Ph is phenyl and Ph-OH is p-hydroxyphenyl; or R17 is CH3 and R18 is H; or R17 and R18 taken together are -CH2CH2CH2-; or -N(R17)-CH(R18)COOH taken together is -NHCH2CONHCH2COOH; and pharmaceutically acceptable salts thereof; with the further provisos that: (a) when n is 2, R14 is other than hydrogen; (b) the sum of m and n is not greater than 10; (c) the sum of p and q is not greater than 10; (d) when X is a bond the sum of m and n is from 5 to 10; (e) when X' is a bond the sum of p and q is from 4 to 9; (f) when R4 is Cl or F, the C-1 position is saturated; and (g) when R9 is =CH2, R10 is other than a second bond between positions C-16 and C-17; excepting the following compounds: 21-(3-Carboxy-1-oxopropoxy)-6.alpha.-fluoro-17.alpha.-hydroxy-16.alpha.-methyl-pregna-1,3,9(11)triene-3,20-dione, sodium salt; 21-(3-carboxy-1-oxopropoxy)-17.alpha.-hydroxy-16.beta.-methylpregna-1,4,9-(11)triene-3,20-dione; 21-(3-carboxy-1-oxopropoxy)-17.alpha.-hydroxy-l6.alpha.-methylpregna-1,4,9 (11)triene-3,20-dione, sodium salt; 21-(3-carboxy-1-oxopropoxy)-17.alpha.-hydroxy-16.alpha.-methylpregna-4,9(11)-diene-3,20-dione, sodium salt; N-methyltaurine amide of 17.alpha.-hydroxypregna-4,9(11)diene-3,20-dione-21-hemisuberate, sodium salt; N-methyltaurine amide of 17.alpha.-hydroxypregna-1,4,9(11)triene-6.alpha.-3,20-dione-21-hemisuberate, sodium salt. |
| priorityDate | 1984-03-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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