FI114708B - 17-desoksikortikosteroidi-21-[O]-karboksyylihappoestereitä, menetelmä niiden valmistamiseksi ja niitä sisältäviä lääkkeitä - Google Patents

17-desoksikortikosteroidi-21-[O]-karboksyylihappoestereitä, menetelmä niiden valmistamiseksi ja niitä sisältäviä lääkkeitä Download PDF

Info

Publication number: FI114708B
Authority: FI; Finland
Prior art keywords: acid; alkyl; eller; group; iii
Prior art date: 1994-09-20

Application number

FI954394A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI954394L (fi

FI954394A0 (fi

Inventor

Ulrich Stache

Hans-Georg Alpermann

Manfred Bohn

Original Assignee

Hoechst Ag

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.)

1994-09-20

Filing date

1995-09-18

Publication date

2004-12-15

1995-09-18 Application filed by Hoechst Ag filed Critical Hoechst Ag

1995-09-18 Publication of FI954394A0 publication Critical patent/FI954394A0/fi

1996-03-21 Publication of FI954394L publication Critical patent/FI954394L/fi

2004-12-15 Application granted granted Critical

2004-12-15 Publication of FI114708B publication Critical patent/FI114708B/fi

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title claims description 11
239000003814 drug Substances 0.000 title claims description 6
229940079593 drug Drugs 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
125000003118 aryl group Chemical group 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 59
150000002148 esters Chemical class 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 17
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 12
150000008064 anhydrides Chemical class 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 8
125000005208 trialkylammonium group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004185 ester group Chemical group 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
150000001734 carboxylic acid salts Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 4
150000001340 alkali metals Chemical class 0.000 claims 2
150000001768 cations Chemical class 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
230000021523 carboxylation Effects 0.000 claims 1
238000006473 carboxylation reaction Methods 0.000 claims 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
210000000653 nervous system Anatomy 0.000 claims 1
239000000843 powder Substances 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 abstract description 10
229910052757 nitrogen Inorganic materials 0.000 abstract description 5
229910052760 oxygen Inorganic materials 0.000 abstract description 4
150000003839 salts Chemical class 0.000 abstract description 3
125000002947 alkylene group Chemical group 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
238000004809 thin layer chromatography Methods 0.000 description 49
238000004949 mass spectrometry Methods 0.000 description 41
239000000047 product Substances 0.000 description 35
239000000243 solution Substances 0.000 description 31
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-1 biphenylyl Chemical group 0.000 description 24
238000003756 stirring Methods 0.000 description 24
239000007795 chemical reaction product Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
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230000008018 melting Effects 0.000 description 19
238000002844 melting Methods 0.000 description 19
239000000203 mixture Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
238000010626 work up procedure Methods 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
230000003110 anti-inflammatory effect Effects 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
150000001735 carboxylic acids Chemical class 0.000 description 9
230000032050 esterification Effects 0.000 description 9
238000005886 esterification reaction Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 9
230000009885 systemic effect Effects 0.000 description 9
AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 8
230000000144 pharmacologic effect Effects 0.000 description 8
238000000746 purification Methods 0.000 description 8
238000012360 testing method Methods 0.000 description 8
238000002955 isolation Methods 0.000 description 7
238000001665 trituration Methods 0.000 description 7
DMJDEZUEYXVYNO-DHZHZOJOSA-N (e)-3-(4-phenylphenyl)prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C1=CC=CC=C1 DMJDEZUEYXVYNO-DHZHZOJOSA-N 0.000 description 6
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
229930016911 cinnamic acid Natural products 0.000 description 6
235000013985 cinnamic acid Nutrition 0.000 description 6
GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 description 6
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
230000000699 topical effect Effects 0.000 description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 4
PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 4
HJBWJAPEBGSQPR-GQCTYLIASA-N 3,4-dimethoxycinnamic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1OC HJBWJAPEBGSQPR-GQCTYLIASA-N 0.000 description 4
MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 4
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 4
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239000002585 base Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 4
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 4
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239000012074 organic phase Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229940049953 phenylacetate Drugs 0.000 description 4
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
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 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
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125000002252 acyl group Chemical group 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
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230000037396 body weight Effects 0.000 description 3
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238000002474 experimental method Methods 0.000 description 3
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XJHGAJLIKDAOPE-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=CC=C1 XJHGAJLIKDAOPE-UHFFFAOYSA-N 0.000 description 2
GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 description 2
CGOJOQBYEAVATL-UHFFFAOYSA-N 3-(4-methoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=C(C=CC(Cl)=O)C=C1 CGOJOQBYEAVATL-UHFFFAOYSA-N 0.000 description 2
NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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CLOXAWYNXXEWBT-UHFFFAOYSA-N tert-butyl n-(3-oxocyclopentyl)carbamate Chemical group CC(C)(C)OC(=O)NC1CCC(=O)C1 CLOXAWYNXXEWBT-UHFFFAOYSA-N 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
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UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0007—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 not substituted in position 17 alfa
- C07J5/0015—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 not substituted in position 17 alfa not substituted in position 16
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
- 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)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI954394A 1994-09-20 1995-09-18 17-desoksikortikosteroidi-21-[O]-karboksyylihappoestereitä, menetelmä niiden valmistamiseksi ja niitä sisältäviä lääkkeitä FI114708B (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4433374A DE4433374A1 (de)	1994-09-20	1994-09-20	17-Desoxi-corticosteroid-21-/O/-Carbonsäure- ester, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE4433374		1994-09-20

Publications (3)

Publication Number	Publication Date
FI954394A0 FI954394A0 (fi)	1995-09-18
FI954394L FI954394L (fi)	1996-03-21
FI114708B true FI114708B (fi)	2004-12-15

Family

ID=6528610

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI954394A FI114708B (fi)	1994-09-20	1995-09-18	17-desoksikortikosteroidi-21-[O]-karboksyylihappoestereitä, menetelmä niiden valmistamiseksi ja niitä sisältäviä lääkkeitä

Country Status (24)

Country	Link
US (1)	US5824670A (cs)
EP (1)	EP0708111B1 (cs)
JP (1)	JP3902255B2 (cs)
KR (1)	KR100406627B1 (cs)
CN (1)	CN1056151C (cs)
AT (1)	ATE188480T1 (cs)
AU (1)	AU695710B2 (cs)
CA (1)	CA2158610C (cs)
CZ (1)	CZ288297B6 (cs)
DE (2)	DE4433374A1 (cs)
DK (1)	DK0708111T3 (cs)
ES (1)	ES2140596T3 (cs)
FI (1)	FI114708B (cs)
GR (1)	GR3032688T3 (cs)
HU (1)	HU217438B (cs)
IL (1)	IL115331A (cs)
NO (1)	NO305210B1 (cs)
NZ (1)	NZ280038A (cs)
PL (1)	PL186071B1 (cs)
PT (1)	PT708111E (cs)
RU (1)	RU2161624C2 (cs)
SI (1)	SI9500295B (cs)
TW (1)	TW424094B (cs)
ZA (1)	ZA957877B (cs)

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RU2180216C2 (ru) *	2000-03-13	2002-03-10	Открытое акционерное общество "Биосинтез"	Препарат, обладающий антимикробным и регенерирующим действием
US20130211069A1 (en)	2010-07-20	2013-08-15	Taro Pharmaceutical Industries Ltd.	Process for the preparation of 17-desoxy-corticosteroids
US12209988B2 (en)	2019-05-24	2025-01-28	Electronics And Telecommunications Research Institute	Sensor and method of manufacturing the same

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Publication number	Priority date	Publication date	Assignee	Title
US2755292A (en) *	1952-01-21	1956-07-17	Organon Labor Ltd	Phenyl propionate of testosterone
US2783226A (en) *	1955-02-03	1957-02-26	Schering Corp	Esters of cortical hormones
ES229413A1 (es) *	1956-06-22	1956-11-01	Francisco Vismara S P A	UN PROCEDIMIENTO PARA LA PREPARACIoN DE COMPUESTOS ESTEROIDALES QUE CONTENGAN UN GRUPO CEToLICO EN LA CADENA LATERAL
DE1131668B (de) *	1959-07-16	1962-06-20	Leo Ab	Verfahren zur Herstellung von Estern von Corticosteroid-Hormonen
CH495969A (de) *	1965-11-09	1970-09-15	Schering Ag	Verfahren zur Herstellung neuer 21-Ester von 16a-Methyl-21-hydroxy- 1,4-steroiden
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FR2342738A1 (fr) *	1976-03-02	1977-09-30	Roussel Uclaf	Nouveaux derives halogenes de la serie du 16a-methyl pregnane
DE2617655C2 (de) *	1976-04-21	1984-11-08	F. Hoffmann-La Roche & Co Ag, Basel	Kortikoide, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE2645104C2 (de) *	1976-10-04	1986-04-24	Schering AG, 1000 Berlin und 4709 Bergkamen	11β-Hydroxy-1,4,8-pregnatrien-3,20-dion-Derivate und Verfahren zu ihrer Herstellung
FR2381065A2 (fr) *	1977-02-22	1978-09-15	Roussel Uclaf	Nouveaux derives halogenes de la serie du 16 a-methyl pregnane
US4086254A (en) *	1977-04-13	1978-04-25	The Upjohn Company	Photocleavable steroids
LU77457A1 (cs) *	1977-05-31	1979-01-19
US4377573A (en) *	1978-01-06	1983-03-22	Leveen Harry H	Method of control of gastrointestinal bleeding
DE2817988A1 (de) *	1978-04-25	1979-11-08	Hoechst Ag	Corticoid 17-alkylcarbonate und verfahren zu deren herstellung
DE2920726A1 (de) *	1979-05-18	1980-11-27	Schering Ag	Neue kortikoide, ihre herstellung und verwendung
EP0039369B1 (en) *	1980-05-02	1983-06-15	Schering Corporation	Beclomethasone ester solvates, process for their preparation, and preparation of a formulation
CY1359A (en) *	1981-02-02	1987-08-07	Schering Corp	Aromatic heterocyclic esters of steroids, their preparation and pharmaceutical compositions containing them
SE8303031D0 (sv) *	1983-05-30	1983-05-30	Leo Ab	Improved steroid esters preparation
US4910191A (en) *	1988-06-28	1990-03-20	Merrell Dow Pharmaceuticals Inc.	19-substituted progesterone derivatives useful as 19-hydroxylase inhibitors
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ZA912235B (en) *	1990-04-02	1991-12-24	Merrell Dow Pharma	Haloethyl-substituted steroidal enzyme inhibitors

1994
- 1994-09-20 DE DE4433374A patent/DE4433374A1/de not_active Withdrawn
1995
- 1995-09-08 TW TW084109384A patent/TW424094B/zh not_active IP Right Cessation
- 1995-09-15 ES ES95114511T patent/ES2140596T3/es not_active Expired - Lifetime
- 1995-09-15 DE DE59507565T patent/DE59507565D1/de not_active Expired - Lifetime
- 1995-09-15 EP EP95114511A patent/EP0708111B1/de not_active Expired - Lifetime
- 1995-09-15 DK DK95114511T patent/DK0708111T3/da active
- 1995-09-15 PT PT95114511T patent/PT708111E/pt unknown
- 1995-09-15 AT AT95114511T patent/ATE188480T1/de active
- 1995-09-18 FI FI954394A patent/FI114708B/fi not_active IP Right Cessation
- 1995-09-18 AU AU31728/95A patent/AU695710B2/en not_active Ceased
- 1995-09-18 IL IL11533195A patent/IL115331A/en not_active IP Right Cessation
- 1995-09-18 US US08/529,668 patent/US5824670A/en not_active Expired - Lifetime
- 1995-09-18 CN CN95116294A patent/CN1056151C/zh not_active Expired - Fee Related
- 1995-09-18 NZ NZ280038A patent/NZ280038A/en not_active IP Right Cessation
- 1995-09-18 CZ CZ19952425A patent/CZ288297B6/cs not_active IP Right Cessation
- 1995-09-19 HU HU9502735A patent/HU217438B/hu not_active IP Right Cessation
- 1995-09-19 NO NO953695A patent/NO305210B1/no not_active IP Right Cessation
- 1995-09-19 JP JP23939895A patent/JP3902255B2/ja not_active Expired - Fee Related
- 1995-09-19 RU RU95116371/04A patent/RU2161624C2/ru not_active IP Right Cessation
- 1995-09-19 PL PL95310544A patent/PL186071B1/pl not_active IP Right Cessation
- 1995-09-19 CA CA002158610A patent/CA2158610C/en not_active Expired - Fee Related
- 1995-09-19 ZA ZA957877A patent/ZA957877B/xx unknown
- 1995-09-20 KR KR1019950030850A patent/KR100406627B1/ko not_active Expired - Fee Related
- 1995-09-20 SI SI9500295A patent/SI9500295B/sl unknown
2000
- 2000-02-18 GR GR20000400386T patent/GR3032688T3/el unknown

Also Published As

Publication number	Publication date
GR3032688T3 (en)	2000-06-30
SI9500295B (en)	2001-12-31
NO953695D0 (no)	1995-09-19
NO953695L (no)	1996-03-21
NZ280038A (en)	1997-03-24
EP0708111B1 (de)	2000-01-05
AU3172895A (en)	1996-04-04
PL310544A1 (en)	1996-04-01
HU217438B (hu)	2000-01-28
CN1056151C (zh)	2000-09-06
CA2158610A1 (en)	1996-03-21
IL115331A (en)	2002-07-25
PL186071B1 (pl)	2003-10-31
IL115331A0 (en)	1995-12-31
HU9502735D0 (en)	1995-11-28
KR960010681A (ko)	1996-04-20
NO305210B1 (no)	1999-04-19
ZA957877B (en)	1996-04-03
KR100406627B1 (ko)	2004-02-19
US5824670A (en)	1998-10-20
JPH0899992A (ja)	1996-04-16
SI9500295A (en)	1996-04-30
DE59507565D1 (de)	2000-02-10
CA2158610C (en)	2007-07-17
CZ288297B6 (en)	2001-05-16
HUT72969A (en)	1996-06-28
ATE188480T1 (de)	2000-01-15
EP0708111A1 (de)	1996-04-24
RU2161624C2 (ru)	2001-01-10
AU695710B2 (en)	1998-08-20
CN1124250A (zh)	1996-06-12
JP3902255B2 (ja)	2007-04-04
PT708111E (pt)	2000-04-28
CZ242595A3 (en)	1996-04-17
FI954394L (fi)	1996-03-21
DE4433374A1 (de)	1996-03-21
ES2140596T3 (es)	2000-03-01
FI954394A0 (fi)	1995-09-18
DK0708111T3 (da)	2000-06-13
TW424094B (en)	2001-03-01

Legal Events

Date	Code	Title	Description
2015-04-22	MM	Patent lapsed

Publication	Publication Date	Title
FI113871B (fi)	2004-06-30	Menetelmä tulehduksen vastaisten kortikosteroidi-17-alkyylikarbonaatti-21-[O]-karboksyylihappo- ja hiilihappoestereiden valmistamiseksi
US5462933A (en)	1995-10-31	Modified bile acid conjugates, and their use as pharmaceuticals
AU2008265898B2 (en)	2013-11-28	Androstane and pregnane steroids with potent allosteric GABA receptor chloride ionophore modulating properties
AU679551B2 (en)	1997-07-03	Corticoid 17,21-dicarboxylic esters and cortiscosteroid 17-carboxylic ester 21-carbonic esters, processes for their preparation and pharmaceuticals containing these compounds
JP5872897B2 (ja)	2016-03-01	新規のコレスト−４−エン−３−オンオキシム誘導体、それを含む医薬組成物及び調製方法
UA79229C2 (en)	2007-06-11	3-nitrogen-6,7-dioxygen steroids and uses related thereto
EA001401B1 (ru)	2001-02-26	ЛАКТОНОВЫЕ ПРОИЗВОДНЫЕ 17β-КАРБОКСИ, КАРБОТИО И АМИД АНДРОСТАНОВ
RU2060997C1 (ru)	1996-05-27	Замещенные кортикоид-17-алкилкарбонаты, способ получения замещенных кортикоид-17-алкилкарбонатов
ES2271090T3 (es)	2007-04-16	Metodo para la preparacion de 21-hidroxi-6,19-oxidoprogesterona (21oh-60p).
KR100450854B1 (ko)	2004-12-16	α-17치환체가없는신규의프레그난유도체,이들의의약용도,제조방법,및이의중간체및관련화합물
JPS59231054A (ja)	1984-12-25	Ｌ−５−ヒドロキシトリプトフアンの新規なジペプチド類およびそれらを製造する方法並びにそれらジペプチド類を含む薬剤
EP0412907B1 (fr)	1994-11-09	Nouveaux esters d'acides organiques avec des alcools dérivés de 19-nor stéroides et leurs sels, leur procédé de préparation et les intermédiaires de ce procédé, leur application à titre de médicaments et les compositions les renfermant
RU2161624C2 (ru)	2001-01-10	Сложный 17-дезокси-кортикоид-21-эфир карбоновой кислоты, способы его получения, лекарственное средство
JPH07501790A (ja)	1995-02-23	５−アルファレダクターゼ阻害剤としてのインドール誘導体
JPH0368039B2 (cs)	1991-10-25
MXPA94006548A (en)	2002-05-09	17-deoxycorticosteroid-21-[o]carboxylic esters, processes for their preparation and pharmaceuticals containing these compounds