DE2534051A1 - 17 alpha, 21-diester von 17 alpha, 21-dihydroxysteroidderivaten, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, worin diese enthalten sind - Google Patents
17 alpha, 21-diester von 17 alpha, 21-dihydroxysteroidderivaten, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, worin diese enthalten sindInfo
- Publication number
- DE2534051A1 DE2534051A1 DE19752534051 DE2534051A DE2534051A1 DE 2534051 A1 DE2534051 A1 DE 2534051A1 DE 19752534051 DE19752534051 DE 19752534051 DE 2534051 A DE2534051 A DE 2534051A DE 2534051 A1 DE2534051 A1 DE 2534051A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- hydroxy
- methyl
- diene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
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- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960005359 propylparaben sodium Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- IXMINYBUNCWGER-UHFFFAOYSA-M sodium;4-propoxycarbonylphenolate Chemical compound [Na+].CCCOC(=O)C1=CC=C([O-])C=C1 IXMINYBUNCWGER-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0088—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0061—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16
- C07J5/0069—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33786/74A GB1516095A (en) | 1974-07-31 | 1974-07-31 | 17,21-diesters of 17alpha,21-dihydroxy-steroids of the pregnane series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2534051A1 true DE2534051A1 (de) | 1976-02-19 |
Family
ID=10357423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752534051 Withdrawn DE2534051A1 (de) | 1974-07-31 | 1975-07-30 | 17 alpha, 21-diester von 17 alpha, 21-dihydroxysteroidderivaten, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, worin diese enthalten sind |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6835724B2 (en) | 1993-10-05 | 2004-12-28 | Aventis Pharma Deutschland Gmbh | Corticoid 17,21-dicarboxylic esters and corticosteroid 17-carboxylic ester 21-carbonic esters, processes for their preparation and pharmaceuticals containing these compounds |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4456602A (en) * | 1982-08-23 | 1984-06-26 | The Upjohn Company | Amine containing ester prodrugs of corticosteroids |
| US4443440A (en) * | 1982-08-30 | 1984-04-17 | The Upjohn Company | Amine containing ester prodrugs of corticosteroids |
| FR2600653B1 (fr) * | 1986-06-24 | 1988-12-16 | Pasteur Strasbourg Universite | Composes de synthese associative d'acides amines soufres ou non soufres avec des derives du d-4 pregnene 3,20-dione ou avec des derives du d-1,4 pregnadiene 3,20-dione aux proprietes glucocorticoides et anti-inflammatoires, procedes d'obtention, compositions pharmaceutiques les contenant. proprietes pharmacologiques et applications |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1044212B (it) * | 1971-03-17 | 1980-03-20 | Sigma Tau Ind Farmaceuti | Esteri del besametazone e betametazone |
| GB1440063A (en) * | 1972-08-11 | 1976-06-23 | Glaxo Lab Ltd | 17alpha-esters of 17alpha,21-dihydroxy-20-oxo-steroids |
-
1974
- 1974-07-31 GB GB33786/74A patent/GB1516095A/en not_active Expired
-
1975
- 1975-07-30 DE DE19752534051 patent/DE2534051A1/de not_active Withdrawn
- 1975-07-30 DK DK346975AA patent/DK139303B/da unknown
- 1975-07-30 SE SE7508654A patent/SE7508654L/xx unknown
- 1975-07-30 JP JP50092137A patent/JPS51125059A/ja active Pending
- 1975-07-30 NL NL7509075A patent/NL7509075A/xx not_active Application Discontinuation
- 1975-07-30 BE BE158780A patent/BE831931A/xx unknown
- 1975-07-30 ZA ZA00754907A patent/ZA754907B/xx unknown
- 1975-07-30 CA CA232,579A patent/CA1058610A/en not_active Expired
- 1975-07-30 IE IE1708/75A patent/IE42124B1/en unknown
- 1975-07-30 CH CH996575A patent/CH615442A5/de not_active IP Right Cessation
- 1975-07-30 FR FR7523787A patent/FR2280383A1/fr active Granted
- 1975-07-30 ES ES439852A patent/ES439852A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6835724B2 (en) | 1993-10-05 | 2004-12-28 | Aventis Pharma Deutschland Gmbh | Corticoid 17,21-dicarboxylic esters and corticosteroid 17-carboxylic ester 21-carbonic esters, processes for their preparation and pharmaceuticals containing these compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| BE831931A (fr) | 1976-01-30 |
| NL7509075A (nl) | 1976-02-03 |
| ZA754907B (en) | 1976-07-28 |
| SE7508654L (sv) | 1976-02-02 |
| JPS51125059A (en) | 1976-11-01 |
| AU8353175A (en) | 1977-02-03 |
| ES439852A1 (es) | 1977-03-01 |
| CA1058610A (en) | 1979-07-17 |
| DK139303C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-06 |
| IE42124L (en) | 1976-01-31 |
| FR2280383B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-06 |
| DK346975A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-02-01 |
| FR2280383A1 (fr) | 1976-02-27 |
| GB1516095A (en) | 1978-06-28 |
| CH615442A5 (en) | 1980-01-31 |
| IE42124B1 (en) | 1980-06-04 |
| DK139303B (da) | 1979-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |