FI113864B - Förfarande för framställning av indolderivat användbara som inhibitorer för steroid- 5alfa-reduktas - Google Patents
Förfarande för framställning av indolderivat användbara som inhibitorer för steroid- 5alfa-reduktas Download PDFInfo
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- FI113864B FI113864B FI955707A FI955707A FI113864B FI 113864 B FI113864 B FI 113864B FI 955707 A FI955707 A FI 955707A FI 955707 A FI955707 A FI 955707A FI 113864 B FI113864 B FI 113864B
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000012679 serum free medium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
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- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
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- 238000010998 test method Methods 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- WBNZLIDKEHELSQ-UHFFFAOYSA-N 1-(1,1-dimethoxypentyl)-4-ethylbenzene Chemical compound CCCCC(OC)(OC)C1=CC=C(CC)C=C1 WBNZLIDKEHELSQ-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- GZNBEOIHTLULAV-UHFFFAOYSA-N 2-[2,2-bis(4-chlorophenyl)-1,3-benzodioxol-5-yl]-1-(1h-indol-3-yl)ethanone Chemical compound C1=CC(Cl)=CC=C1C1(C=2C=CC(Cl)=CC=2)OC2=CC(CC(=O)C=3C4=CC=CC=C4NC=3)=CC=C2O1 GZNBEOIHTLULAV-UHFFFAOYSA-N 0.000 description 1
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ATZHGRNFEFVDDJ-UHFFFAOYSA-N 4-propylbenzoic acid Chemical compound CCCC1=CC=C(C(O)=O)C=C1 ATZHGRNFEFVDDJ-UHFFFAOYSA-N 0.000 description 1
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- 229940122815 Aromatase inhibitor Drugs 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 241000400611 Eucalyptus deanei Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
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- 238000007171 acid catalysis Methods 0.000 description 1
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- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
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- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
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- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 229960001389 doxazosin Drugs 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- GEEHMSFNGGISSO-UHFFFAOYSA-N ethyl 4-[3-[2-[2,2-bis(4-chlorophenyl)-1,3-benzodioxol-5-yl]acetyl]indol-1-yl]butanoate Chemical compound C12=CC=CC=C2N(CCCC(=O)OCC)C=C1C(=O)CC(C=C1O2)=CC=C1OC2(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 GEEHMSFNGGISSO-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940076701 hydro 35 Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000002390 hyperplastic effect Effects 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- UYDPSGULERCPSZ-UHFFFAOYSA-N methyl 2-[2,2-bis(4-chlorophenyl)-1,3-benzodioxol-5-yl]acetate Chemical compound O1C2=CC(CC(=O)OC)=CC=C2OC1(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 UYDPSGULERCPSZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- HWWVAHCWJLGKLW-UHFFFAOYSA-N n,n-dimethylhydroxylamine;hydron;chloride Chemical compound Cl.CN(C)O HWWVAHCWJLGKLW-UHFFFAOYSA-N 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229940095585 testosterone-5-alpha reductase inhibitors for benign prostatic hypertrophy Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (4)
1. Förfarande för framställning av terapeutiskt användbara indolderivat med formeln (I) och farmaceutiskt 5 godtagbara bassalter därav, - " (CHJäCOjH där
15 R1 är C3-Ce-alkyl, och R2 är C2-C4-alkyl, kännetecknat därav, att man avspjälker den esterbildande gruppen R4 frän en förening med formeln: 2 0 β1 : ,·. 25 I ; : : (CH^COjR4 • 1 1 \‘,Y där R4 är en esterbildande grupp, och R1 och R2 betecknar » t · ‘ samma som ovan.
2. Förfarande enligt patentkrav 1, k ä n n e - • 30 tecknat därav, att man framställer 4-(3-[(2-n- ·...1 butyl-2- [ 4-etyl] f enyl-1,3-bensodioxolan-5-yl) metylkarb- onyl] indol-l-yl) butansyra eller 4-(3-[ (2-n-butyl-2-[4-n-,···, propyl] fenyl-1,3-bensodioxolan-5-yl)metylkarbonyl] indol-l- yl) butansyra eller ett farmaceutiskt godtagbart bassalt *. 35 därav. • · • · 113864
3. Förening med formeln: • cr/^n ..... 1
4 (CH2)3C02R4 10 där R4 är Ci-C6-alkyl och R1 och R2 betecknar sarama sora i patentkrav 1, eller ett bassalt därav. 1 · · » · · » t · * « · • · • · • · »
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB939311008A GB9311008D0 (en) | 1993-05-28 | 1993-05-28 | Indoles |
GB9311008 | 1993-05-28 | ||
GB9317529 | 1993-08-20 | ||
GB939317529A GB9317529D0 (en) | 1993-05-28 | 1993-08-20 | Indoles |
EP9401760 | 1994-05-26 | ||
PCT/EP1994/001760 WO1994027990A1 (en) | 1993-05-28 | 1994-05-26 | INDOLE DERIVATIVES AS STEROID 5α-REDUCTASE INHIBITORS |
Publications (3)
Publication Number | Publication Date |
---|---|
FI955707A FI955707A (sv) | 1995-11-27 |
FI955707A0 FI955707A0 (sv) | 1995-11-27 |
FI113864B true FI113864B (sv) | 2004-06-30 |
Family
ID=26302960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI955707A FI113864B (sv) | 1993-05-28 | 1995-11-27 | Förfarande för framställning av indolderivat användbara som inhibitorer för steroid- 5alfa-reduktas |
Country Status (14)
Country | Link |
---|---|
US (2) | US5696146A (sv) |
EP (1) | EP0700395B1 (sv) |
JP (1) | JP2757969B2 (sv) |
AT (1) | ATE154352T1 (sv) |
AU (1) | AU6930494A (sv) |
CA (1) | CA2163778C (sv) |
DE (1) | DE69403793T2 (sv) |
DK (1) | DK0700395T3 (sv) |
ES (1) | ES2102863T3 (sv) |
FI (1) | FI113864B (sv) |
GR (1) | GR3024366T3 (sv) |
HU (1) | HU9501935D0 (sv) |
IL (1) | IL109728A0 (sv) |
WO (1) | WO1994027990A1 (sv) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9204365D0 (en) * | 1992-02-28 | 1992-04-08 | Pfizer Ltd | Indoles |
GB9317096D0 (en) * | 1993-08-17 | 1993-09-29 | Pfizer Ltd | Indoles |
WO2008042898A2 (en) | 2006-10-02 | 2008-04-10 | Cortendo Invest, Ab | Ketoconazole enantiomer in humans |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9011335D0 (en) * | 1990-05-21 | 1990-07-11 | Fujisawa Pharmaceutical Co | Indolebutyric acid derivatives and process for preparation thereof |
GB9204365D0 (en) * | 1992-02-28 | 1992-04-08 | Pfizer Ltd | Indoles |
GB9317096D0 (en) * | 1993-08-17 | 1993-09-29 | Pfizer Ltd | Indoles |
-
1994
- 1994-05-23 IL IL10972894A patent/IL109728A0/xx unknown
- 1994-05-26 WO PCT/EP1994/001760 patent/WO1994027990A1/en active IP Right Grant
- 1994-05-26 DK DK94917676.2T patent/DK0700395T3/da active
- 1994-05-26 CA CA002163778A patent/CA2163778C/en not_active Expired - Fee Related
- 1994-05-26 EP EP94917676A patent/EP0700395B1/en not_active Expired - Lifetime
- 1994-05-26 US US08/553,589 patent/US5696146A/en not_active Expired - Fee Related
- 1994-05-26 HU HU9501935A patent/HU9501935D0/hu unknown
- 1994-05-26 AT AT94917676T patent/ATE154352T1/de not_active IP Right Cessation
- 1994-05-26 AU AU69304/94A patent/AU6930494A/en not_active Abandoned
- 1994-05-26 ES ES94917676T patent/ES2102863T3/es not_active Expired - Lifetime
- 1994-05-26 JP JP7500251A patent/JP2757969B2/ja not_active Expired - Lifetime
- 1994-05-26 DE DE69403793T patent/DE69403793T2/de not_active Expired - Fee Related
-
1995
- 1995-11-27 FI FI955707A patent/FI113864B/sv not_active IP Right Cessation
-
1997
- 1997-08-06 GR GR970402013T patent/GR3024366T3/el unknown
- 1997-12-02 US US08/982,735 patent/US5922747A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0700395A1 (en) | 1996-03-13 |
JP2757969B2 (ja) | 1998-05-25 |
CA2163778C (en) | 1999-04-27 |
EP0700395B1 (en) | 1997-06-11 |
ES2102863T3 (es) | 1997-08-01 |
GR3024366T3 (en) | 1997-11-28 |
IL109728A0 (en) | 1994-08-26 |
DE69403793D1 (de) | 1997-07-17 |
FI955707A (sv) | 1995-11-27 |
US5922747A (en) | 1999-07-13 |
DE69403793T2 (de) | 1997-09-25 |
WO1994027990A1 (en) | 1994-12-08 |
AU6930494A (en) | 1994-12-20 |
US5696146A (en) | 1997-12-09 |
JPH08506350A (ja) | 1996-07-09 |
FI955707A0 (sv) | 1995-11-27 |
HU9501935D0 (en) | 1995-09-28 |
CA2163778A1 (en) | 1994-12-08 |
DK0700395T3 (da) | 1997-10-13 |
ATE154352T1 (de) | 1997-06-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MA | Patent expired |