IL22709A - 21-esters of pregnane derivatives and a process for their preparation - Google Patents
21-esters of pregnane derivatives and a process for their preparationInfo
- Publication number
- IL22709A IL22709A IL2270964A IL2270964A IL22709A IL 22709 A IL22709 A IL 22709A IL 2270964 A IL2270964 A IL 2270964A IL 2270964 A IL2270964 A IL 2270964A IL 22709 A IL22709 A IL 22709A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- fact
- preparation
- stage
- chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 13
- 150000003126 pregnane derivatives Chemical class 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 22
- 229960005205 prednisolone Drugs 0.000 claims description 6
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane group Chemical group [C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229960004544 cortisone Drugs 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229960004618 prednisone Drugs 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- NGSMAXPULGPQNT-UHFFFAOYSA-N 7,7-dimethylbicyclo[2.2.1]heptane Chemical compound C1CC2CCC1C2(C)C NGSMAXPULGPQNT-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001887 cortisones Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- -1 steroid alcohols Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
C O H E N Z E D E K P I S B A C H RE G PAT ENT ATTO RN EYS 1169 T E A V I V P A T E N T S D E S I G N S O D I A N C E s esters of steroid alcohols have already More they have a very favourable effect which permits spacing the intervals between their Among these prednisolone is of particular especially Another object of the invention is a process for new esters of the above general This process is characterized essentially by the fact that a functional derivative of the such as earboxylic for the acid cho a en is reacted with the cortisone derivative in the presence of a tertiar base such as the presence or absence of an organic The may be for the treatment of radicular acute or chronic acute or chronic rheumatic infections as well as are also useful in the treatment of conditions tory infectious fibroses and it is anticipated that they can be used fo topical action on the skin and the mucous and especially for the treatment of inflammatory infections of the of the ihe product of the general formula I are used locally by topical app cation on ski membranes and presented They may the form of injectable ampul ae or prepared as in multiple flasks dose table coated eye washes and pulverized topical in they will be used intraarticular The useful ranges between 1 and 40 grams per adult as a of the of le the in being spaced protracted respec The pharmaceutical as injectable solutions or eye washes topical powders are prepared by the usual The following examples will invention bette They have no limiting Stage Preparation of acid chlo 2 g of apocamphane are mixed with 10 of thionyl chloride and the mixture is left in contact for 16 hours at ambient the excess thionyl chloride is removed by heating on an oil bath under the residue is taken up with benzene and then evaporated to acid chloride is obtained in the form of a yellow residue it that is in the following The starting can be obtained according to the method by 61 Stage Preparation of chloride To the in the previous a solution of 3 g of prednisolone in 10 the reaction mixture is at th of pyridine is slowly with temperature or 4 The 3 tion mixture is poured into a mixture of 10 of 3 hydrochloric in 100 of a the precipitate is then washed with normal hydrochloric saturated solution of sodium and again with water until the water washings are and the precipitate is dried under vacuum at it is purified b stallization in ethanol and g of obtained in the a colourless uble in acetone and slightly soluble in alcohol and benzenej insoluble in dilute aqueous and it at 260 its rotatory powe This product is described in the Example acid chloride is prepared as in example by mixing g of acid with 10 of thionyl This is solved in cm of anhydrous and g prednisolone and of kept over are The reaction exothermic and a limpid solution is rapidly It is stirred for 20 hours at ambient The chloroform solution is washed with dilute hydrochloric The product is dried and evaporated under The residue is in prednisolone identical with tha in is Example acid chloride is prepared as in example by mixing of acid with 6 of thionyl This dissolved in of anydrous and this solution is drop by to a suspension of 2 g of predinolone in 5 ca 3 of occurs by precipitation of Stirring is for 10 minutes at then for hours at ambient The reaction mixture poured into an excess of dilute hydrochloric The desired product It is filtered and treated as in example Example Preparation of To a solution of acid chloride from g of apocamp ane carboxylic acid and thlonyl in 20 of 2 of dexamethasone and cm of anhydrous with reaction is is continued for 15 hours at temperature then the mixture is washed with dilute hydrochloric The chloroform layer is dried and evaporated under is obtained which is in the form of colourless which are insoluble in and soluble in chloroform and methylene The spectrum accords wit the This product is not described in the Exampl Preparation of The reaction is carried out in the same manner as f Starting with g of and acid chloride by treating g of acid with cm of thion l g of are This after is in the form of colourless crystals insoluble in and soluble in chloroform and methylene the spectrum accords with the This product is not described in the Pile 12798 Example of Stage As The chloride of acid is prepared according to the above described starting with g of acid and cc of thionyl Stage g of prednisone are in the manner described with the chloride obtained in Stage There are obtained g of prednisone The product is obtained in the form insoluble in water and in dilute soluble in most of the conventional organic This compound not been described in Example T Preparation Cortisone Stage The chloride of acid is prepared according to the above described starting with g of the acid and cc of thionyl Stage g of cortisone are treated in the manner described above with the chloride obtained in Stage There is obtained g of The product is obtained in the form of colorless insoluble in water and in dilute soluble in most Example Preparation of Stage The chloride of lic acid is prepared according to the above described starting with g of the acid and cc of thionyl Stage g of Cortisol are treated according the above described procedure the chloride obtained in Stage There are obtained g of The produc is obtained the form of colorless insoluble in water and in dilute soluble in most of the common organic λ max 242 The compound not beed described in the Example Preparation of Stage A The chloride of acid is prepared according to the above described procedure starting with g of the acid and cc of thionyl Stage g are treated according to the above described procedure with the chloride obtained in Stage There obtained of 9 The product is obtained in the form of colorless insoluble in water and in dilute soluble Pile 12798 Example Preparation of Stage The chloride of acid was prepared according to the above described starting with g of the acid and thionyl Stage g of oro prednisolone are treated according to the above described procedure with the chloride obtained i stage here are obtained g of which is obtained in the form of colorless insoluble in insoluble in dilute and soluble in most of the common organic λ 14 The product has not been described in the Example Preparation of Stag The chloride of acid was prepared according to the procedure described starting with g of the acid and cc o thionyl Stage g of are treated with the chloride obtained in Stage There are obtained g of product is obtained in the form of colorless insoluble in water and in dilute soluble in most of the common organic 12798 Example Preparation of Stage The chloride of acid is prepared according to the procedure described starting with g of the acid cc of thionyl Stage g of tflamcinolone are treated according to the procedure described above with the chloride obtained in Stage There are obtained g of which is obtained in the form of colorless insoluble in insoluble in dilute acids and soluble in most of the common organic λ max 259 ω ε The product is not described in the insufficientOCRQuality
Claims (1)
1. particularly described and ascertained nattire of our invention and in manner same is to declare that what we claim steroids ified in the of the general formula conventional the he any pregnane structure also conventional and or combinations of any of attached to the nucleus i positions to such as free or substituted hydroxyl in 11 or groups 3 or halogen atoms in 6 or groups in 6 or double bonds in 1 or 4 or Betaaet Process for the preparation according to claims 1 to characterized by the fact that a functional derivative of respective acid is reacted with pregnane derivative in the presence of a tertiary Process according Claim characterized by the fact that the functional derivative of acid used is the Process according to Claim characterized from the by the fact that the tertiary base is selected of diraethylaniline and tri Process according to characterized by the fact that the reaction is effected in the sence of an organic Process for the preparation of characterized by the fact that a functional derivative of acid reacted with prednisolone in the presence of and the desired ester is The pharmaceutical containing a according to Claims 1 to 13 a ceutical DATED Attorneys for Applicants insufficientOCRQuality
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR959163A FR3316M (en) | 1964-01-02 | 1964-01-02 | New drug in particular for the treatment of inflammatory manifestations of rheumatic, arthritic or infectious origin. |
| FR966962A FR1512324A (en) | 1964-01-02 | 1964-03-11 | New esters in 21 of cortisone derivatives and method of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL22709A true IL22709A (en) | 1969-02-27 |
Family
ID=26205184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2270964A IL22709A (en) | 1964-01-02 | 1964-12-31 | 21-esters of pregnane derivatives and a process for their preparation |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE657319A (en) |
| BR (1) | BR6465428D0 (en) |
| CH (1) | CH436282A (en) |
| DE (1) | DE1468892B1 (en) |
| DK (1) | DK112236B (en) |
| FR (2) | FR3316M (en) |
| GB (1) | GB1087729A (en) |
| IL (1) | IL22709A (en) |
| NL (2) | NL6414704A (en) |
| SE (1) | SE318274B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1439605A (en) * | 1972-07-14 | 1976-06-16 | Akzo Nv | 2beta-hydroxy-3-alpha-amino-steroids and derivatives thereof and the processes for their preparation |
-
0
- BE BE657319D patent/BE657319A/xx unknown
- NL NL122978D patent/NL122978C/xx active
-
1964
- 1964-01-02 FR FR959163A patent/FR3316M/en active Active
- 1964-03-11 FR FR966962A patent/FR1512324A/en not_active Expired
- 1964-12-15 DE DE19641468892 patent/DE1468892B1/en not_active Withdrawn
- 1964-12-17 NL NL6414704A patent/NL6414704A/xx unknown
- 1964-12-17 BR BR16542864A patent/BR6465428D0/en unknown
- 1964-12-18 SE SE1542164A patent/SE318274B/xx unknown
- 1964-12-18 DK DK622064A patent/DK112236B/en unknown
- 1964-12-18 CH CH1636164A patent/CH436282A/en unknown
- 1964-12-21 GB GB51833/64A patent/GB1087729A/en not_active Expired
- 1964-12-31 IL IL2270964A patent/IL22709A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH436282A (en) | 1967-05-31 |
| BE657319A (en) | |
| FR1512324A (en) | 1968-02-09 |
| DK112236B (en) | 1968-11-25 |
| FR3316M (en) | 1965-05-17 |
| NL122978C (en) | |
| SE318274B (en) | 1969-12-08 |
| BR6465428D0 (en) | 1973-08-07 |
| DE1468892B1 (en) | 1970-03-12 |
| GB1087729A (en) | 1967-10-18 |
| NL6414704A (en) | 1965-07-05 |
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