FI57757C - Foerfarande foer framstaellning av terapeutiskt anvaendbara tioxantenderivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbara tioxantenderivat Download PDF

Info

Publication number: FI57757C
Authority: FI; Finland
Prior art keywords: thioxanthene; formula; trifluoromethyl; therapeutic; fluoro
Prior art date: 1973-11-30

Application number

FI3395/74A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI339574A7 (fr

FI57757B (fi

Inventor

Georg Ujvari

Peter Bregnedal Hansen

Original Assignee

Kefalas As

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.)

1973-11-30

Filing date

1974-11-22

Publication date

1980-10-10

1974-11-22 Application filed by Kefalas As filed Critical Kefalas As

1975-05-31 Publication of FI339574A7 publication Critical patent/FI339574A7/fi

1980-06-30 Application granted granted Critical

1980-06-30 Publication of FI57757B publication Critical patent/FI57757B/fi

1980-10-10 Publication of FI57757C publication Critical patent/FI57757C/fi

Links

230000001225 therapeutic effect Effects 0.000 title 3
150000001875 compounds Chemical class 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 10
150000005075 thioxanthenes Chemical class 0.000 claims description 7
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229940054058 antipsychotic thioxanthene derivative Drugs 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000012535 impurity Substances 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
150000003839 salts Chemical class 0.000 description 21
239000000243 solution Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
231100000252 nontoxic Toxicity 0.000 description 7
230000003000 nontoxic effect Effects 0.000 description 7
-1 theophylline acetic acids Chemical class 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229960001344 methylphenidate Drugs 0.000 description 6
239000002775 capsule Substances 0.000 description 5
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 4
229960002419 flupentixol Drugs 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
WFPIAZLQTJBIFN-BLLMUTORSA-N 2-[4-[(3e)-3-(2-chlorothioxanthen-9-ylidene)propyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CC\C=C/1C2=CC(Cl)=CC=C2SC2=CC=CC=C2\1 WFPIAZLQTJBIFN-BLLMUTORSA-N 0.000 description 3
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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 3
235000021314 Palmitic acid Nutrition 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229960001552 chlorprothixene Drugs 0.000 description 3
NJMYODHXAKYRHW-DVZOWYKESA-N cis-flupenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C2/1 NJMYODHXAKYRHW-DVZOWYKESA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
WSPOMRSOLSGNFJ-AUWJEWJLSA-N (Z)-chlorprothixene Chemical compound C1=C(Cl)C=C2C(=C/CCN(C)C)\C3=CC=CC=C3SC2=C1 WSPOMRSOLSGNFJ-AUWJEWJLSA-N 0.000 description 2
PZQVJGHDMPYSGG-UHFFFAOYSA-N 3-(2-chloro-9H-thioxanthen-9-yl)-N,N-dimethylprop-2-en-1-amine Chemical compound C1=C(Cl)C=C2C(C=CCN(C)C)C3=CC=CC=C3SC2=C1 PZQVJGHDMPYSGG-UHFFFAOYSA-N 0.000 description 2
CMCQSHMMGIWGKY-UHFFFAOYSA-N 3-[6-fluoro-2-(trifluoromethyl)-9H-thioxanthen-9-yl]-N,N-dimethylprop-2-en-1-amine Chemical compound C1=C(C(F)(F)F)C=C2C(C=CCN(C)C)C3=CC=C(F)C=C3SC2=C1 CMCQSHMMGIWGKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
244000223760 Cinnamomum zeylanicum Species 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
238000003556 assay Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
235000017803 cinnamon Nutrition 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
KZTWONRVIPPDKH-UHFFFAOYSA-N hydroxyethyl piperidine Natural products OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
IJWXZHLWKYGRPY-UHFFFAOYSA-N 3-(9H-thioxanthen-10-ylidene)propan-1-amine Chemical class C1=CC=C2S(=CCCN)C3=CC=CC=C3CC2=C1 IJWXZHLWKYGRPY-UHFFFAOYSA-N 0.000 description 1
ZDGGCIXEWFPFAH-UHFFFAOYSA-N 6-fluoro-2-(trifluoromethyl)thioxanthen-9-one Chemical compound C1=C(C(F)(F)F)C=C2C(=O)C3=CC=C(F)C=C3SC2=C1 ZDGGCIXEWFPFAH-UHFFFAOYSA-N 0.000 description 1
GRFZWXGOHAQNGF-UHFFFAOYSA-N 6-fluoro-9-prop-2-enylidene-2-(trifluoromethyl)thioxanthene Chemical compound FC(F)(F)C1=CC=C2SC3=CC(F)=CC=C3C(=CC=C)C2=C1 GRFZWXGOHAQNGF-UHFFFAOYSA-N 0.000 description 1
IWNPWQRBFNOGHM-UHFFFAOYSA-N 9h-thioxanthen-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3SC2=C1 IWNPWQRBFNOGHM-UHFFFAOYSA-N 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001494479 Pecora Species 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229940025084 amphetamine Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000004885 piperazines Chemical group 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
229960005013 tiotixene Drugs 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/20—Thioxanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Hydrogenated Pyridines (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Plural Heterocyclic Compounds (AREA)

FI3395/74A 1973-11-30 1974-11-22 Foerfarande foer framstaellning av terapeutiskt anvaendbara tioxantenderivat FI57757C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB5575973		1973-11-30
GB55759/73A GB1480593A (en)	1973-11-30	1973-11-30	Xanthene and thioxanthene derivatives having pharmaceutical activity

Publications (3)

Publication Number	Publication Date
FI339574A7 FI339574A7 (fr)	1975-05-31
FI57757B FI57757B (fi)	1980-06-30
FI57757C true FI57757C (fi)	1980-10-10

Family

ID=10474807

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI3395/74A FI57757C (fi)	1973-11-30	1974-11-22	Foerfarande foer framstaellning av terapeutiskt anvaendbara tioxantenderivat

Country Status (16)

Country	Link
US (1)	US3951961A (fr)
JP (1)	JPS5093973A (fr)
AT (1)	AT336013B (fr)
BE (1)	BE822710A (fr)
CA (1)	CA1048038A (fr)
CH (1)	CH605895A5 (fr)
DE (1)	DE2456098C3 (fr)
DK (1)	DK137575B (fr)
ES (1)	ES432439A1 (fr)
FI (1)	FI57757C (fr)
FR (1)	FR2253510B1 (fr)
GB (1)	GB1480593A (fr)
IE (1)	IE40261B1 (fr)
NL (1)	NL7415177A (fr)
NO (1)	NO140795C (fr)
SE (1)	SE415659B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE409860B (sv) *	1977-07-04	1979-09-10	Astra Laekemedel Ab	En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningar
SE7909514L (sv) *	1979-11-16	1981-05-17	Astra Laekemedel Ab	Nya halofenyl-pyridyl-allylaminderivat
CA2267500A1 (fr)	1996-10-04	1998-04-16	Novo Nordisk A/S	Composes azaheterocycliques n-substitues
CN102786511B (zh) *	2011-05-18	2014-10-15	重庆圣华曦药业股份有限公司	一种制备盐酸氟哌噻吨中间体的改进方法
EP2998303B1 (fr)	2014-09-17	2018-06-13	B & G Partners, LLC	Derivées de phenothiazine et procédés pour traiter des tumeurs
CN115850232B (zh) *	2023-02-16	2023-05-26	广州佳途科技股份有限公司	一种氟哌噻吨ep杂质h的制备方法及其应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE557002A (fr) *	1956-07-09
US3192204A (en) *	1960-03-07	1965-06-29	Smith Kline French Lab	Trifluoromethylthiaxanthene and -xanthene derivatives
US3282930A (en) *	1962-08-17	1966-11-01	Smith Kline French Lab	Hydroxyalkylenepiperazine derivatives and analogs thereof
US3310553A (en) *	1962-09-25	1967-03-21	Pfizer & Co C	Alkylated thioxathenesulfonamides
US3157658A (en) *	1963-07-05	1964-11-17	Searle & Co	1-carbalkoxy-4-(9-xanthenyl) piperazines and related compounds
US3681346A (en) *	1969-06-20	1972-08-01	Kefalas As	{60 -isomer of the decanoic acid ester of 10-{8 3,-(4-hydroxyethyl-1-piperazinyl)propylidene{9 -2-trifluoro-methyl thiaxanthene, acid addition salts thereof, method of use and compositions

1973
- 1973-11-30 GB GB55759/73A patent/GB1480593A/en not_active Expired
1974
- 1974-11-19 IE IE2383/74A patent/IE40261B1/en unknown
- 1974-11-21 US US05/525,967 patent/US3951961A/en not_active Expired - Lifetime
- 1974-11-21 NL NL7415177A patent/NL7415177A/xx not_active Application Discontinuation
- 1974-11-22 FI FI3395/74A patent/FI57757C/fi active
- 1974-11-27 DE DE2456098A patent/DE2456098C3/de not_active Expired
- 1974-11-28 JP JP49135963A patent/JPS5093973A/ja active Pending
- 1974-11-28 BE BE150952A patent/BE822710A/fr unknown
- 1974-11-28 AT AT952174A patent/AT336013B/de not_active IP Right Cessation
- 1974-11-29 CH CH1588074A patent/CH605895A5/xx not_active IP Right Cessation
- 1974-11-29 ES ES432439A patent/ES432439A1/es not_active Expired
- 1974-11-29 SE SE7414983A patent/SE415659B/xx unknown
- 1974-11-29 NO NO744310A patent/NO140795C/no unknown
- 1974-11-29 CA CA214,934A patent/CA1048038A/fr not_active Expired
- 1974-12-02 DK DK624774AA patent/DK137575B/da unknown
- 1974-12-02 FR FR7439427A patent/FR2253510B1/fr not_active Expired

Also Published As

Publication number	Publication date
FR2253510A1 (fr)	1975-07-04
DE2456098B2 (de)	1978-04-27
GB1480593A (en)	1977-07-20
DK137575C (fr)	1978-09-11
NO140795C (no)	1979-11-14
CA1048038A (fr)	1979-02-06
SE415659B (sv)	1980-10-20
IE40261B1 (en)	1979-04-25
DE2456098A1 (de)	1975-06-05
SE7414983L (fr)	1975-06-02
FI339574A7 (fr)	1975-05-31
CH605895A5 (fr)	1978-10-13
US3951961A (en)	1976-04-20
DK137575B (da)	1978-03-28
AU7561574A (en)	1976-05-27
IE40261L (en)	1975-05-30
NO140795B (no)	1979-08-06
DE2456098C3 (de)	1979-01-18
ES432439A1 (es)	1976-11-16
BE822710A (fr)	1975-05-28
FR2253510B1 (fr)	1977-12-09
AT336013B (de)	1977-04-12
JPS5093973A (fr)	1975-07-26
ATA952174A (de)	1976-08-15
FI57757B (fi)	1980-06-30
NO744310L (fr)	1975-06-23
DK624774A (fr)	1975-07-28
NL7415177A (nl)	1975-06-03

Publication	Publication Date	Title
US4430343A (en)	1984-02-07	Benzimidazole derivatives, process for the preparation thereof and pharmaceutical composition containing the same
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
DE1795183B1 (de)	1972-07-20	5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel
NO138565B (no)	1978-06-19	Analogifremgangsmaate ved fremstilling av terapeutisk aktive piperazinyl-propyl-1,2,4-triazolinonderivater
DE1470125C3 (de)	1980-07-10	4-Oxo-13,8-triazaspiro [4,5] decane
US3388128A (en)	1968-06-11	Substituted 1, 4-diazabicyclo [4. 4. 9] decanes
HUT58316A (en)	1992-02-28	Process for producing carbostiryl derivatives and pharmaceutical compositions containing them
FI57757C (fi)	1980-10-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara tioxantenderivat
US3966930A (en)	1976-06-29	Phenothiazine derivatives, compositions thereof and methods of preparation thereof
DE3586411T2 (de)	1993-01-07	Dopamin-antagoniste.
DE2719211A1 (de)	1977-11-03	Arylalkylpiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2707268A1 (de)	1978-08-31	Indol-3-carbaldehyd-oxime und verfahren zu ihrer herstellung
US4042695A (en)	1977-08-16	Thiaxanthene derivatives, compositions thereof and methods of treating therewith
DE2707270A1 (de)	1978-08-24	Pyrazolo-diazepine und verfahren zu ihrer herstellung
US3963727A (en)	1976-06-15	1,2 Disubstituted benzimidazole derivatives
US4029790A (en)	1977-06-14	1-Benzoyl-2 or 4 [2-(4-phenyl-piperazino)-ethyl]-piperidines
DE2757422A1 (de)	1978-06-29	Verfahren zur herstellung von neuen n-substituierten 2-phenyl-benzo eckige klammer auf b eckige klammer zu thiophen- 3-amin-derivaten
US2928835A (en)	1960-03-15	New esters
US3657440A (en)	1972-04-18	Aminoalkyl-spirocycloalkanes as analgetic agents
US3764684A (en)	1973-10-09	Novel indolobenzazepine derivatives, useful as tranquilizers
US4022896A (en)	1977-05-10	Xanthene and thioxanthene compositions and method of treating
US3466290A (en)	1969-09-09	9,10-dihydro-4h-benzo(4,5)cyclohepta(1,2-b)thiophene ethers
DE2359359A1 (de)	1974-06-27	Fluor-substituierte thioxanthene und verfahren zu deren herstellung sowie diese enthaltende pharmazeutische mittel
US3205134A (en)	1965-09-07	Antidepressant benzilates of piperazinoalkanols
EP0000693A1 (fr)	1979-02-21	Dérivés d'aminophénoxyméthyl-2-morpholine, procédé pour leur préparation et médicaments les contenant