IL42250A - 6alpha-methylprednisolone-21-metasulphobenzoate preparation process and pharmaceutical compositions - Google Patents
6alpha-methylprednisolone-21-metasulphobenzoate preparation process and pharmaceutical compositionsInfo
- Publication number
- IL42250A IL42250A IL42250A IL4225073A IL42250A IL 42250 A IL42250 A IL 42250A IL 42250 A IL42250 A IL 42250A IL 4225073 A IL4225073 A IL 4225073A IL 42250 A IL42250 A IL 42250A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- product
- lithium
- methyl
- methylprednisolone
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 claims abstract 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical group [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- 229940102223 injectable solution Drugs 0.000 claims 2
- 150000002641 lithium Chemical group 0.000 claims 2
- VHRSUDSXCMQTMA-UHFFFAOYSA-N 11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound CC12C=CC(=O)C=C1C(C)CC1C2C(O)CC2(C)C(O)(C(=O)CO)CCC21 VHRSUDSXCMQTMA-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- 229940096112 prednisol Drugs 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 2
- -1 alkali metal salts Chemical class 0.000 abstract description 2
- 239000003456 ion exchange resin Substances 0.000 abstract description 2
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 2
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 abstract 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000003470 adrenal cortex hormone Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 206010001497 Agitation Diseases 0.000 description 3
- 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 3
- 238000013019 agitation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940112482 entsol Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 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 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7218035A FR2193576B1 (sv) | 1972-05-19 | 1972-05-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42250A0 IL42250A0 (en) | 1973-07-30 |
| IL42250A true IL42250A (en) | 1977-06-30 |
Family
ID=9098837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42250A IL42250A (en) | 1972-05-19 | 1973-05-11 | 6alpha-methylprednisolone-21-metasulphobenzoate preparation process and pharmaceutical compositions |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5212777B2 (sv) |
| AT (1) | AT325221B (sv) |
| AU (1) | AU473292B2 (sv) |
| BE (1) | BE799615A (sv) |
| CA (1) | CA977746A (sv) |
| CH (1) | CH572068A5 (sv) |
| CS (1) | CS165956B2 (sv) |
| DD (1) | DD104787A5 (sv) |
| DK (1) | DK133683B (sv) |
| EG (1) | EG11080A (sv) |
| ES (1) | ES414870A1 (sv) |
| FI (1) | FI52588C (sv) |
| FR (1) | FR2193576B1 (sv) |
| GB (1) | GB1375357A (sv) |
| HU (1) | HU165993B (sv) |
| IE (1) | IE37657B1 (sv) |
| IL (1) | IL42250A (sv) |
| NL (1) | NL7306962A (sv) |
| NO (1) | NO138148C (sv) |
| PH (1) | PH12351A (sv) |
| PL (1) | PL85506B1 (sv) |
| SE (1) | SE399711B (sv) |
| SU (1) | SU493961A3 (sv) |
| YU (1) | YU35037B (sv) |
| ZA (1) | ZA733340B (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5112816A (ja) * | 1975-04-03 | 1976-01-31 | Wakao Kanao | Tairubaripurekyasutokonkuriitono seizohoho |
| JPS51122118A (en) * | 1975-04-15 | 1976-10-26 | Wakao Kanao | Production of tiled precast concrete |
| US4588718A (en) * | 1984-03-28 | 1986-05-13 | The Upjohn Company | Carboxy containing ester prodrugs of corticosteroids |
| US4948533A (en) * | 1984-03-28 | 1990-08-14 | The Upjohn Company | 11a-hydroxy steroid diester |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3089881A (en) * | 1957-10-29 | 1963-05-14 | Schering Corp | Sulfocarboxylic acid esters of hydroxylated steroids |
-
1972
- 1972-05-19 FR FR7218035A patent/FR2193576B1/fr not_active Expired
-
1973
- 1973-05-04 CH CH638173A patent/CH572068A5/xx not_active IP Right Cessation
- 1973-05-10 PH PH7314601A patent/PH12351A/en unknown
- 1973-05-11 IL IL42250A patent/IL42250A/en unknown
- 1973-05-15 YU YU1278/73A patent/YU35037B/xx unknown
- 1973-05-15 CS CS3446A patent/CS165956B2/cs unknown
- 1973-05-15 FI FI731564A patent/FI52588C/sv active
- 1973-05-16 BE BE131184A patent/BE799615A/xx unknown
- 1973-05-17 PL PL1973162627A patent/PL85506B1/pl unknown
- 1973-05-17 ZA ZA733340A patent/ZA733340B/xx unknown
- 1973-05-17 HU HURO730A patent/HU165993B/hu unknown
- 1973-05-17 SE SE7306996A patent/SE399711B/sv unknown
- 1973-05-18 SU SU1916475A patent/SU493961A3/ru active
- 1973-05-18 NL NL7306962A patent/NL7306962A/xx unknown
- 1973-05-18 CA CA171,864A patent/CA977746A/en not_active Expired
- 1973-05-18 ES ES414870A patent/ES414870A1/es not_active Expired
- 1973-05-18 JP JP48054774A patent/JPS5212777B2/ja not_active Expired
- 1973-05-18 DD DD170919A patent/DD104787A5/xx unknown
- 1973-05-18 AU AU55900/73A patent/AU473292B2/en not_active Expired
- 1973-05-18 NO NO2058/73A patent/NO138148C/no unknown
- 1973-05-19 EG EG186/73A patent/EG11080A/xx active
- 1973-05-21 IE IE811/73A patent/IE37657B1/xx unknown
- 1973-05-21 AT AT441473A patent/AT325221B/de not_active IP Right Cessation
- 1973-05-21 GB GB2401373A patent/GB1375357A/en not_active Expired
- 1973-05-21 DK DK277473AA patent/DK133683B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5212777B2 (sv) | 1977-04-09 |
| YU127873A (en) | 1979-12-31 |
| FR2193576A1 (sv) | 1974-02-22 |
| IE37657L (en) | 1973-11-19 |
| DD104787A5 (sv) | 1974-03-20 |
| NL7306962A (sv) | 1973-11-21 |
| EG11080A (en) | 1977-04-30 |
| JPS4948653A (sv) | 1974-05-11 |
| BE799615A (fr) | 1973-11-16 |
| CA977746A (en) | 1975-11-11 |
| ZA733340B (en) | 1974-11-27 |
| AT325221B (de) | 1975-10-10 |
| DK133683C (sv) | 1976-11-15 |
| SE399711B (sv) | 1978-02-27 |
| GB1375357A (sv) | 1974-11-27 |
| DE2325358B2 (de) | 1976-01-29 |
| DK133683B (da) | 1976-06-28 |
| ES414870A1 (es) | 1976-05-01 |
| CS165956B2 (sv) | 1975-12-22 |
| FR2193576B1 (sv) | 1975-08-08 |
| AU473292B2 (en) | 1976-06-17 |
| NO138148B (no) | 1978-04-03 |
| FI52588C (sv) | 1977-10-10 |
| IL42250A0 (en) | 1973-07-30 |
| IE37657B1 (en) | 1977-09-14 |
| DE2325358A1 (de) | 1973-11-29 |
| FI52588B (sv) | 1977-06-30 |
| PL85506B1 (sv) | 1976-04-30 |
| SU493961A3 (ru) | 1975-11-28 |
| YU35037B (en) | 1980-06-30 |
| CH572068A5 (sv) | 1976-01-30 |
| PH12351A (en) | 1979-01-29 |
| HU165993B (sv) | 1974-12-28 |
| AU5590073A (en) | 1974-11-21 |
| NO138148C (no) | 1978-07-12 |
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