NO135790B - - Google Patents
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- Publication number
- NO135790B NO135790B NO217371A NO217371A NO135790B NO 135790 B NO135790 B NO 135790B NO 217371 A NO217371 A NO 217371A NO 217371 A NO217371 A NO 217371A NO 135790 B NO135790 B NO 135790B
- Authority
- NO
- Norway
- Prior art keywords
- triamcinolone acetonide
- acid
- ester
- thionyl chloride
- added
- Prior art date
Links
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical class C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims description 29
- 229960002117 triamcinolone acetonide Drugs 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 13
- 150000001263 acyl chlorides Chemical class 0.000 claims description 4
- 230000001741 anti-phlogistic effect Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- -1 sulphate ions Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- UONVJZSIMUCBQK-UHFFFAOYSA-N 7-acetamidoheptanoic acid Chemical compound CC(=O)NCCCCCCC(O)=O UONVJZSIMUCBQK-UHFFFAOYSA-N 0.000 description 2
- MWCXFMZMNBCOJN-UHFFFAOYSA-N 7-benzamidoheptanoic acid Chemical compound OC(=O)CCCCCCNC(=O)C1=CC=CC=C1 MWCXFMZMNBCOJN-UHFFFAOYSA-N 0.000 description 2
- JJGPOXVRGPROSW-UHFFFAOYSA-N 8-acetamidooctanoic acid Chemical compound CC(=O)NCCCCCCCC(O)=O JJGPOXVRGPROSW-UHFFFAOYSA-N 0.000 description 2
- KTDXBSZMCLIHCO-UHFFFAOYSA-N 8-benzamidooctanoic acid Chemical compound OC(=O)CCCCCCCNC(=O)C1=CC=CC=C1 KTDXBSZMCLIHCO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960004582 acexamic acid Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960005294 triamcinolone Drugs 0.000 description 2
- 229940070710 valerate Drugs 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PZIVHOLHABBQKU-UHFFFAOYSA-N 2-benzamidopentanoic acid Chemical compound CCCC(C(O)=O)NC(=O)C1=CC=CC=C1 PZIVHOLHABBQKU-UHFFFAOYSA-N 0.000 description 1
- CCEBPEVKSYSXIR-UHFFFAOYSA-N 3-benzamido-2-methylpropanoic acid Chemical compound OC(=O)C(C)CNC(=O)C1=CC=CC=C1 CCEBPEVKSYSXIR-UHFFFAOYSA-N 0.000 description 1
- CWXYHOHYCJXYFQ-UHFFFAOYSA-N Betamipron Chemical compound OC(=O)CCNC(=O)C1=CC=CC=C1 CWXYHOHYCJXYFQ-UHFFFAOYSA-N 0.000 description 1
- KTHDTJVBEPMMGL-UHFFFAOYSA-N N-Acetyl-DL-alanine Chemical compound OC(=O)C(C)NC(C)=O KTHDTJVBEPMMGL-UHFFFAOYSA-N 0.000 description 1
- LJLLAWRMBZNPMO-UHFFFAOYSA-N N-acetyl-beta-alanine Chemical compound CC(=O)NCCC(O)=O LJLLAWRMBZNPMO-UHFFFAOYSA-N 0.000 description 1
- BSYFPUSAWVWWDG-UHFFFAOYSA-N N-acetylnorvaline Chemical compound CCCC(C(O)=O)NC(C)=O BSYFPUSAWVWWDG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229960004311 betamethasone valerate Drugs 0.000 description 1
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate 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)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000003096 thymolvtic effect Effects 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
-
- 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
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- 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
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2572170A IT1045260B (it) | 1970-06-09 | 1970-06-09 | Estere del triamcinolone acetonide per l impiego antiflogistico topico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135790B true NO135790B (cs) | 1977-02-21 |
| NO135790C NO135790C (cs) | 1977-06-08 |
Family
ID=11217531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO217371A NO135790C (cs) | 1970-06-09 | 1971-06-08 |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE768315A (cs) |
| IT (1) | IT1045260B (cs) |
| NL (1) | NL156049B (cs) |
| NO (1) | NO135790C (cs) |
| SE (1) | SE379769B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116829A (en) * | 1990-04-23 | 1992-05-26 | Kao Corporation | Steroid compounds |
-
1970
- 1970-06-09 IT IT2572170A patent/IT1045260B/it active
-
1971
- 1971-05-26 NL NL7107246A patent/NL156049B/xx not_active IP Right Cessation
- 1971-06-07 SE SE734971A patent/SE379769B/xx unknown
- 1971-06-08 NO NO217371A patent/NO135790C/no unknown
- 1971-06-09 BE BE768315A patent/BE768315A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO135790C (cs) | 1977-06-08 |
| NL156049B (nl) | 1978-03-15 |
| NL7107246A (cs) | 1971-12-13 |
| IT1045260B (it) | 1980-05-10 |
| SE379769B (cs) | 1975-10-20 |
| BE768315A (fr) | 1971-11-03 |
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