BG60799B2 - Ароматни хетероциклени стероидни естери,получаването им и фармацевтични състави,които ги съдържат - Google Patents

Ароматни хетероциклени стероидни естери,получаването им и фармацевтични състави,които ги съдържат Download PDF

Info

Publication number: BG60799B2
Authority: BG; Bulgaria
Prior art keywords: methyl; furoate; pregnadiene; dione; fluorine
Prior art date: 1981-02-02

Application number

BG098562A

Other languages

Bulgarian (bg)

English (en)

Inventor

Elliot Shapiro

Original Assignee

Schering Corporation

Priority date (The priority date 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 date listed.)

1981-02-02

Filing date

1994-02-24

Publication date

1996-03-29

1994-02-24 Application filed by Schering Corporation filed Critical Schering Corporation

1996-03-29 Publication of BG60799B2 publication Critical patent/BG60799B2/bg

Links

238000002360 preparation method Methods 0.000 title claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
-1 steroid esters Chemical class 0.000 title claims description 52
125000003118 aryl group Chemical group 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 143
238000000034 method Methods 0.000 claims abstract description 42
239000000203 mixture Substances 0.000 claims description 50
229910052739 hydrogen Inorganic materials 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 33
239000000460 chlorine Substances 0.000 claims description 32
239000011737 fluorine Substances 0.000 claims description 31
229910052731 fluorine Inorganic materials 0.000 claims description 31
229910052801 chlorine Inorganic materials 0.000 claims description 28
229950005792 tenoate Drugs 0.000 claims description 23
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 22
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 18
239000007858 starting material Substances 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 13
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 12
230000003110 anti-inflammatory effect Effects 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004185 ester group Chemical group 0.000 claims description 6
229950010765 pivalate Drugs 0.000 claims description 6
YYYFRRSYTVJIOE-WWAIPBPMSA-N (2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-3-[[(2S,3S)-2-[[(2R)-1,2-dimethylpyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]-methylamino]-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-5-(4-aminophenyl)-2-methylpentanoic acid Chemical group CC[C@H](C)[C@H](NC(=O)[C@@]1(C)CCCN1C)C(=O)N(C)[C@H](C[C@@H](OC(C)=O)c1nc(cs1)C(=O)N[C@H](C[C@H](C)C(O)=O)Cc1ccc(N)cc1)C(C)C YYYFRRSYTVJIOE-WWAIPBPMSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
150000001735 carboxylic acids Chemical class 0.000 claims description 5
238000005658 halogenation reaction Methods 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
125000000118 dimethyl group Chemical class [H]C([H])([H])* 0.000 claims description 4
230000026030 halogenation Effects 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Chemical group 0.000 claims description 4
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 3
229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
239000002260 anti-inflammatory agent Substances 0.000 claims description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
229930002330 retinoic acid Natural products 0.000 claims description 3
229960001727 tretinoin Drugs 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
QIEPWCSVQYUPIY-LEKSSAKUSA-N Delta(1)-progesterone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 QIEPWCSVQYUPIY-LEKSSAKUSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 2
239000004593 Epoxy Substances 0.000 claims 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000004054 inflammatory process Effects 0.000 abstract description 4
125000001424 substituent group Chemical group 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 219
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
239000002904 solvent Substances 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
238000001819 mass spectrum Methods 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
150000002500 ions Chemical class 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
239000012043 crude product Substances 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
238000012746 preparative thin layer chromatography Methods 0.000 description 22
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 20
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
238000003756 stirring Methods 0.000 description 18
238000004809 thin layer chromatography Methods 0.000 description 18
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000012153 distilled water Substances 0.000 description 12
239000012071 phase Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 11
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
239000007787 solid Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
238000007429 general method Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
238000005886 esterification reaction Methods 0.000 description 8
238000001914 filtration Methods 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
125000002252 acyl group Chemical group 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
230000032050 esterification Effects 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
239000012359 Methanesulfonyl chloride Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
229940045860 white wax Drugs 0.000 description 4
RKWYVIIRVNFNMM-QEGKIEECSA-N (8s,9r,10s,13r,14s,16r,17s)-17-ethyl-9-fluoro-10,13,16-trimethyl-3,6,7,8,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@H](CC)[C@@]1(C)CC2 RKWYVIIRVNFNMM-QEGKIEECSA-N 0.000 description 3
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
239000006071 cream Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000001747 exhibiting effect Effects 0.000 description 3
BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 3
229940051250 hexylene glycol Drugs 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000001863 hydroxypropyl cellulose Substances 0.000 description 3
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 3
239000006210 lotion Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000002674 ointment Substances 0.000 description 3
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
NBLHTECOWAHOPA-LVUPHWHUSA-N (9r,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,9,11,12-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@@H](CC[C@@]3(C(C(=O)C)=CC=C33)C)C3=CCC21 NBLHTECOWAHOPA-LVUPHWHUSA-N 0.000 description 2
FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 2
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 2
IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 2
YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 2
229920006051 Capron® Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
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 2
150000007942 carboxylates Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003246 corticosteroid Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
229940050176 methyl chloride Drugs 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
229940093625 propylene glycol monostearate Drugs 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000008719 thickening Effects 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
239000003871 white petrolatum Substances 0.000 description 2
HSQDJSAINPPZLR-ZSCHJXSPSA-N (2s)-2,6-diaminohexanoic acid;octadecanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.CCCCCCCCCCCCCCCCCC(O)=O HSQDJSAINPPZLR-ZSCHJXSPSA-N 0.000 description 1
NRQHBNNTBIDSRK-YRNVUSSQSA-N (4e)-4-[(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one Chemical compound C1=CC(OC)=CC=C1\C=C\1C(=O)OC(C)=N/1 NRQHBNNTBIDSRK-YRNVUSSQSA-N 0.000 description 1
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VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical class CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
CCEBPEVKSYSXIR-UHFFFAOYSA-N 3-benzamido-2-methylpropanoic acid Chemical class OC(=O)C(C)CNC(=O)C1=CC=CC=C1 CCEBPEVKSYSXIR-UHFFFAOYSA-N 0.000 description 1
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical class OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
QLVNUZPODFIOGC-UHFFFAOYSA-N 5-bromofuran-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Br)O1 QLVNUZPODFIOGC-UHFFFAOYSA-N 0.000 description 1
IFLKEBSJTZGCJG-UHFFFAOYSA-N 5-methyl-2-thiophenecarboxylic acid Natural products CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 description 1
VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012434 Dermatitis allergic Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
206010014025 Ear swelling Diseases 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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201000004681 Psoriasis Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FPVRUILUEYSIMD-RPRRAYFGSA-N [(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate 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(C)=O)[C@@]1(C)C[C@@H]2O FPVRUILUEYSIMD-RPRRAYFGSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
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150000001253 acrylic acids Chemical class 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
201000008937 atopic dermatitis Diseases 0.000 description 1
239000000022 bacteriostatic agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
229960002537 betamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone 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-DVTGEIKXSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
229940117173 croton oil Drugs 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
229960003657 dexamethasone acetate Drugs 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
CNTIXUGILVWVHR-UHFFFAOYSA-N diphosphoryl chloride Chemical compound ClP(Cl)(=O)OP(Cl)(Cl)=O CNTIXUGILVWVHR-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
210000002257 embryonic structure Anatomy 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003862 glucocorticoid Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229940075529 glyceryl stearate Drugs 0.000 description 1
230000005484 gravity Effects 0.000 description 1
238000009775 high-speed stirring Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
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 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
SSOVKTIUBYUZHC-UHFFFAOYSA-N lithium;tributoxyalumane Chemical compound [Li].CCCCO[Al](OCCCC)OCCCC SSOVKTIUBYUZHC-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000002092 orthoester group Chemical group 0.000 description 1
239000002304 perfume Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000825 pharmaceutical preparation 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
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical compound CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000008213 purified water Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000002207 retinal effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
150000003398 sorbic acids Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- 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
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyridine Compounds (AREA)

BG098562A 1981-02-02 1994-02-24 Ароматни хетероциклени стероидни естери,получаването им и фармацевтични състави,които ги съдържат BG60799B2 (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US23076381A	1981-02-02	1981-02-02

Publications (1)

Publication Number	Publication Date
BG60799B2 true BG60799B2 (bg)	1996-03-29

Family

ID=22866476

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG098562A BG60799B2 (bg)	1981-02-02	1994-02-24	Ароматни хетероциклени стероидни естери,получаването им и фармацевтични състави,които ги съдържат

Country Status (25)

Country	Link
US (1)	US4472393A (no)
EP (1)	EP0057401B1 (no)
JP (1)	JPS57146800A (no)
KR (1)	KR890000761B1 (no)
AT (1)	ATE8790T1 (no)
AU (1)	AU549102B2 (no)
BG (1)	BG60799B2 (no)
CA (1)	CA1177822A (no)
CY (1)	CY1359A (no)
DE (1)	DE3260474D1 (no)
DK (1)	DK162770C (no)
FI (1)	FI78111C (no)
HK (1)	HK68487A (no)
HU (1)	HU188769B (no)
IE (1)	IE52576B1 (no)
IL (1)	IL64885A (no)
KE (1)	KE3694A (no)
MX (1)	MX9203403A (no)
NL (1)	NL930095I2 (no)
NO (2)	NO157020C (no)
NZ (1)	NZ199600A (no)
OA (1)	OA07116A (no)
PH (1)	PH19733A (no)
PT (1)	PT74357B (no)
ZA (1)	ZA82566B (no)

Families Citing this family (119)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5446177A (en) *	1984-12-28	1995-08-29	Alcon Laboratories, Inc.	Anti-inflammatory compounds for ophthalmic use
US4686214A (en) *	1985-10-30	1987-08-11	Alcon Laboratories, Inc.	Anti-inflammatory compounds for ophthalmic use
US4914090A (en) *	1985-11-01	1990-04-03	Schering Corporation	Ophthalmic compositions
IL79661A (en) *	1986-08-08	1991-01-31	Yeda Res & Dev	Antiviral composition containing hypericin or pseudohypericin
US4808610A (en) *	1986-10-02	1989-02-28	Schering Corporation	Mometasone furoate anti-inflammatory cream composition using hexylene glycol
US4775529A (en) *	1987-05-21	1988-10-04	Schering Corporation	Steroid lotion
US6536427B2 (en)	1990-03-02	2003-03-25	Glaxo Group Limited	Inhalation device
TW197380B (no) *	1990-03-02	1993-01-01	Glaxo Group Ltd
SK280967B6 (sk)	1990-03-02	2000-10-09	Glaxo Group Limited	Inhalačný prístroj
PL165803B1 (pl) *	1990-09-10	1995-02-28	Schering Corp	Sposób wytwarzania nowego monohydratu 9a, 21-dichloro-16-a metylo-1,4-pregnadieno-11 ß , 17a-diolo-3,20-diono-17-(2’furanokarboksylanu) PL PL PL PL
DE69231991T2 (de)	1991-06-10	2002-04-04	Schering Corp., Kenilworth	Fluorchlorkohlenwasserstofffreie Aerosolformulierungen
DE69208660T2 (de) †	1991-06-10	1996-07-11	Schering Corp., Kenilworth, N.J.	Fluorchlorkohlenwasserstoffreie aerosolformulierungen
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1982
- 1982-01-25 DE DE8282100490T patent/DE3260474D1/de not_active Expired
- 1982-01-25 CY CY135982A patent/CY1359A/xx unknown
- 1982-01-25 AT AT82100490T patent/ATE8790T1/de active
- 1982-01-25 EP EP82100490A patent/EP0057401B1/en not_active Expired
- 1982-01-28 NO NO820263A patent/NO157020C/no not_active IP Right Cessation
- 1982-01-28 NZ NZ199600A patent/NZ199600A/en unknown
- 1982-01-28 ZA ZA82566A patent/ZA82566B/xx unknown
- 1982-01-28 FI FI820280A patent/FI78111C/fi not_active IP Right Cessation
- 1982-01-28 IL IL64885A patent/IL64885A/xx unknown
- 1982-01-28 DK DK039082A patent/DK162770C/da not_active IP Right Cessation
- 1982-01-28 AU AU79918/82A patent/AU549102B2/en not_active Expired
- 1982-01-29 IE IE207/82A patent/IE52576B1/en not_active IP Right Cessation
- 1982-01-29 JP JP57013191A patent/JPS57146800A/ja active Granted
- 1982-01-29 KR KR8200374A patent/KR890000761B1/ko active
- 1982-01-29 PH PH26804A patent/PH19733A/en unknown
- 1982-01-29 CA CA000395237A patent/CA1177822A/en not_active Expired
- 1982-01-29 PT PT74357A patent/PT74357B/pt unknown
- 1982-02-01 HU HU82295A patent/HU188769B/hu unknown
- 1982-06-03 OA OA57705A patent/OA07116A/xx unknown
- 1982-07-29 US US06/403,276 patent/US4472393A/en not_active Expired - Lifetime
1987
- 1987-02-19 KE KE3694A patent/KE3694A/xx unknown
- 1987-09-24 HK HK684/87A patent/HK68487A/xx not_active IP Right Cessation
1992
- 1992-06-25 MX MX9203403A patent/MX9203403A/es active IP Right Grant
1993
- 1993-06-24 NL NL930095C patent/NL930095I2/nl unknown
1994
- 1994-02-24 BG BG098562A patent/BG60799B2/bg unknown
- 1994-10-07 NO NO1994018C patent/NO1994018I1/no unknown

Also Published As

Publication number	Publication date
NO157020B (no)	1987-09-28
PT74357B (en)	1984-05-30
KR890000761B1 (ko)	1989-04-05
HU188769B (en)	1986-05-28
ATE8790T1 (de)	1984-08-15
MX9203403A (es)	1992-07-01
NO1994018I1 (no)	1994-10-07
IE820207L (en)	1982-08-02
KE3694A (en)	1987-03-13
NZ199600A (en)	1984-09-28
PH19733A (en)	1986-06-17
NL930095I2 (nl)	1994-12-01
DK162770B (da)	1991-12-09
FI78111C (fi)	1989-06-12
HK68487A (en)	1987-10-02
FI820280L (fi)	1982-08-03
IL64885A0 (en)	1982-03-31
IE52576B1 (en)	1987-12-23
DE3260474D1 (en)	1984-09-06
PT74357A (en)	1982-02-01
IL64885A (en)	1985-05-31
AU549102B2 (en)	1986-01-16
NL930095I1 (nl)	1993-10-01
JPS57146800A (en)	1982-09-10
EP0057401B1 (en)	1984-08-01
DK162770C (da)	1992-04-27
NO157020C (no)	1988-01-06
CY1359A (en)	1987-08-07
OA07116A (fr)	1984-03-31
AU7991882A (en)	1982-08-12
CA1177822A (en)	1984-11-13
JPS6360036B2 (no)	1988-11-22
EP0057401A1 (en)	1982-08-11
FI78111B (fi)	1989-02-28
NO820263L (no)	1982-08-03
KR830009138A (ko)	1983-12-17
DK39082A (da)	1982-08-03
ZA82566B (en)	1982-12-29
US4472393A (en)	1984-09-18

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GB1563638A (en)	1980-03-26	21-halogenopregnane compounds
EP0004765A2 (en)	1979-10-17	Corticosteroid anti-inflammatory agents, their use and methods for their preparation
US4185101A (en)	1980-01-22	1,3,5(10),6,8-19-Nor-pregnapentaenes, their use as anti-psoriatic agents, and pharmaceutical formulations useful therefor
US4511511A (en)	1985-04-16	Prednisolone derivatives
US4221786A (en)	1980-09-09	Novel halogenopregnadienes and process for the manufacture thereof
EP0000609B1 (en)	1981-09-23	Novel 19-nor-pregnahexaenes, process for the preparation thereof, and pharmaceutical compositions containing them
DE2756550C2 (de)	1986-10-16	Verfahren zur Herstellung von 3,20-Dioxo-7&alpha;-halogen-4-pregnenen und 1,4-Pregnadienen, 3,20-Dioxo-7&alpha;-chlor und Brom-1,4-pregnadiene und letztere enthaltende Arzneimittel
KR810000311B1 (ko)	1981-04-09	7-할로-3,20-디옥소-1,4-프레그나디엔 및 -4-프레그넨의 제조 방법
KR840000155B1 (ko)	1984-02-22	6α, 9α-디플루오로-16-메틸-프레드니솔론 17, 21-디에스테르의 제조방법
GB1589585A (en)	1981-05-13	12a-halocorticoids
GB1603281A (en)	1981-11-25	Derivatives of 9-fluoroprednisolone
CS199512B2 (cs)	1980-07-31	Způsob výroby kortikoidfi
NO864979L (no)	1986-10-01	Androstan-17 beta-karboksylsyreforbindelser.