DD224591A5 - Verfahren zur herstellung von substituierten phenylalkyl-(piperazinyl oder homopiperazinyl)alkylthiolen - Google Patents

Verfahren zur herstellung von substituierten phenylalkyl-(piperazinyl oder homopiperazinyl)alkylthiolen Download PDF

Info

Publication number: DD224591A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; alkyl; hydrogen; piperazin; dihydrochloride
Prior art date: 1983-05-31

Application number

DD84263572A

Other languages

German (de)

English (en)

Inventor

D Karl Hargrave

John P Devlin

Edward L Barsumian

Original Assignee

Boehringer Ingelheim Ltd

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.)

1983-05-31

Filing date

1984-05-30

Publication date

1985-07-10

1984-05-30 Application filed by Boehringer Ingelheim Ltd filed Critical Boehringer Ingelheim Ltd

1985-07-10 Publication of DD224591A5 publication Critical patent/DD224591A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 62
-1 PIPERAZINYL Chemical class 0.000 title claims description 97
150000001356 alkyl thiols Chemical class 0.000 title abstract description 3
238000004519 manufacturing process Methods 0.000 title description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 58
150000001875 compounds Chemical class 0.000 claims abstract description 41
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
239000001257 hydrogen Substances 0.000 claims abstract description 40
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
150000003839 salts Chemical class 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
150000002431 hydrogen Chemical class 0.000 claims abstract description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 7
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 34
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
230000007062 hydrolysis Effects 0.000 claims description 15
238000006460 hydrolysis reaction Methods 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
231100000252 nontoxic Toxicity 0.000 claims description 8
230000003000 nontoxic effect Effects 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000004953 trihalomethyl group Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
150000001350 alkyl halides Chemical class 0.000 claims description 5
239000012467 final product Substances 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 1
208000026935 allergic disease Diseases 0.000 abstract description 5
238000011282 treatment Methods 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 4
230000001900 immune effect Effects 0.000 abstract description 4
125000004193 piperazinyl group Chemical group 0.000 abstract description 4
230000003266 anti-allergic effect Effects 0.000 abstract description 3
208000027866 inflammatory disease Diseases 0.000 abstract description 3
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
208000026278 immune system disease Diseases 0.000 abstract description 2
230000002757 inflammatory effect Effects 0.000 abstract description 2
125000003884 phenylalkyl group Chemical group 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 111
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 49
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
239000000203 mixture Substances 0.000 description 33
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 28
238000002844 melting Methods 0.000 description 27
230000008018 melting Effects 0.000 description 27
239000000575 pesticide Substances 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
235000019441 ethanol Nutrition 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000010626 work up procedure Methods 0.000 description 12
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 9
239000007787 solid Substances 0.000 description 9
ATLKRPODWOIJSC-UHFFFAOYSA-N carbamothioic s-acid;dihydrochloride Chemical compound Cl.Cl.NC(S)=O ATLKRPODWOIJSC-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000002674 ointment Substances 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000000443 aerosol Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
GSJXJZOWHSTWOX-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]piperazine Chemical compound C1=CC(Cl)=CC=C1CN1CCNCC1 GSJXJZOWHSTWOX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000002775 capsule Substances 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
SPLUIOPIOHZUHU-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(1-phenylethyl)piperazine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1C(C)N1CCN(CCCCl)CC1 SPLUIOPIOHZUHU-UHFFFAOYSA-N 0.000 description 3
LJJRXPXDTAUVQU-UHFFFAOYSA-N 1-butyl-4-isocyanatobenzene Chemical compound CCCCC1=CC=C(N=C=O)C=C1 LJJRXPXDTAUVQU-UHFFFAOYSA-N 0.000 description 3
FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 3
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
235000006708 antioxidants Nutrition 0.000 description 3
229960000686 benzalkonium chloride Drugs 0.000 description 3
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000872 buffer Substances 0.000 description 3
230000001413 cellular effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229960000265 cromoglicic acid Drugs 0.000 description 3
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
210000003630 histaminocyte Anatomy 0.000 description 3
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125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
MUXMKICPRJIZCX-UHFFFAOYSA-N propane-1,1-diol;dihydrochloride Chemical compound Cl.Cl.CCC(O)O MUXMKICPRJIZCX-UHFFFAOYSA-N 0.000 description 3
SUVIGLJNEAMWEG-UHFFFAOYSA-N propyl mercaptan Natural products CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
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229960000278 theophylline Drugs 0.000 description 3
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HJTOTAUIBLSHDI-UHFFFAOYSA-N 1-(2-chloroethyl)-4-[(4-chlorophenyl)methyl]piperazine;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCl)CCN1CC1=CC=C(Cl)C=C1 HJTOTAUIBLSHDI-UHFFFAOYSA-N 0.000 description 2
AWKJOIDAGDJKEV-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(3-phenylpropyl)piperazine;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCl)CCN1CCCC1=CC=CC=C1 AWKJOIDAGDJKEV-UHFFFAOYSA-N 0.000 description 2
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ANLJZMORYZBOLI-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-4-(3-chloropropyl)piperazine;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCl)CCN1CC1=CC=C(Cl)C=C1 ANLJZMORYZBOLI-UHFFFAOYSA-N 0.000 description 2
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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239000012153 distilled water Substances 0.000 description 2
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GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
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235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000010874 in vitro model Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
229960001268 isoetarine Drugs 0.000 description 1
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235000019388 lanolin Nutrition 0.000 description 1
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239000006194 liquid suspension Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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238000005259 measurement Methods 0.000 description 1
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229940098779 methanesulfonic acid Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229940042472 mineral oil Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000065 noncytotoxic Toxicity 0.000 description 1
230000002020 noncytotoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
229940054534 ophthalmic solution Drugs 0.000 description 1
239000002997 ophthalmic solution Substances 0.000 description 1
229960002657 orciprenaline Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229940067107 phenylethyl alcohol Drugs 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
239000003223 protective agent Substances 0.000 description 1
239000002510 pyrogen 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
238000001953 recrystallisation Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
229960002052 salbutamol Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229940001607 sodium bisulfite Drugs 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000011146 sterile filtration Methods 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (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)
Immunology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

DD84263572A 1983-05-31 1984-05-30 Verfahren zur herstellung von substituierten phenylalkyl-(piperazinyl oder homopiperazinyl)alkylthiolen DD224591A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US49918883A	1983-05-31	1983-05-31

Publications (1)

Publication Number	Publication Date
DD224591A5 true DD224591A5 (de)	1985-07-10

Family

ID=23984207

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84263572A DD224591A5 (de)	1983-05-31	1984-05-30	Verfahren zur herstellung von substituierten phenylalkyl-(piperazinyl oder homopiperazinyl)alkylthiolen

Country Status (24)

Country	Link
EP (1)	EP0127182B1 (cs)
JP (1)	JPS59227868A (cs)
KR (1)	KR900001188B1 (cs)
AT (1)	ATE24502T1 (cs)
AU (1)	AU566668B2 (cs)
CA (1)	CA1215979A (cs)
CS (1)	CS245792B2 (cs)
DD (1)	DD224591A5 (cs)
DE (1)	DE3461797D1 (cs)
DK (1)	DK163921C (cs)
ES (1)	ES532930A0 (cs)
FI (1)	FI77238C (cs)
GR (1)	GR82001B (cs)
HU (1)	HU192405B (cs)
IE (1)	IE57841B1 (cs)
IL (1)	IL71970A (cs)
NO (1)	NO169895C (cs)
NZ (1)	NZ208334A (cs)
PH (1)	PH21555A (cs)
PL (1)	PL142332B1 (cs)
PT (1)	PT78667B (cs)
SU (1)	SU1355128A3 (cs)
YU (1)	YU43569B (cs)
ZA (1)	ZA844101B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4692448A (en) *	1984-11-20	1987-09-08	Boehringer Ingelheim Pharmaceuticals, Inc.	Bis(arylpiperazinyl)sulfur compounds
CA2180190A1 (en) *	1995-07-10	1997-01-11	Kazumi Ogata	Benzylpiperazine derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1286198A (fr) *	1961-04-07	1962-03-02	Bayer Ag	Procédé de fabrication d'esters s-alkyliques, à substituants basiques, de l'acide phénylthiocarbamique
GB952142A (en) *	1961-05-26	1964-03-11	Miles Lab	Phenylpiperazinylalkyl carbamates

1984
- 1984-05-29 FI FI842141A patent/FI77238C/fi not_active IP Right Cessation
- 1984-05-29 GR GR74863A patent/GR82001B/el unknown
- 1984-05-30 IE IE1346/84A patent/IE57841B1/en not_active IP Right Cessation
- 1984-05-30 CA CA000455423A patent/CA1215979A/en not_active Expired
- 1984-05-30 ZA ZA844101A patent/ZA844101B/xx unknown
- 1984-05-30 PH PH30739A patent/PH21555A/en unknown
- 1984-05-30 KR KR1019840003003A patent/KR900001188B1/ko not_active Expired
- 1984-05-30 CS CS844059A patent/CS245792B2/cs unknown
- 1984-05-30 DD DD84263572A patent/DD224591A5/de not_active IP Right Cessation
- 1984-05-30 DE DE8484106160T patent/DE3461797D1/de not_active Expired
- 1984-05-30 HU HU842102A patent/HU192405B/hu not_active IP Right Cessation
- 1984-05-30 DK DK268484A patent/DK163921C/da not_active IP Right Cessation
- 1984-05-30 YU YU925/84A patent/YU43569B/xx unknown
- 1984-05-30 IL IL71970A patent/IL71970A/xx unknown
- 1984-05-30 EP EP84106160A patent/EP0127182B1/en not_active Expired
- 1984-05-30 SU SU843745557A patent/SU1355128A3/ru active
- 1984-05-30 AT AT84106160T patent/ATE24502T1/de not_active IP Right Cessation
- 1984-05-30 NO NO842154A patent/NO169895C/no unknown
- 1984-05-30 ES ES532930A patent/ES532930A0/es active Granted
- 1984-05-30 PL PL1984247953A patent/PL142332B1/pl unknown
- 1984-05-31 PT PT78667A patent/PT78667B/pt not_active IP Right Cessation
- 1984-05-31 NZ NZ208334A patent/NZ208334A/en unknown
- 1984-05-31 JP JP59109807A patent/JPS59227868A/ja active Pending
- 1984-05-31 AU AU28878/84A patent/AU566668B2/en not_active Ceased

Also Published As

Publication number	Publication date
GR82001B (cs)	1984-12-12
AU566668B2 (en)	1987-10-29
FI842141A0 (fi)	1984-05-29
PL142332B1 (en)	1987-10-31
NZ208334A (en)	1987-02-20
ATE24502T1 (de)	1987-01-15
ZA844101B (en)	1986-02-26
PT78667B (en)	1986-09-08
IL71970A0 (en)	1984-09-30
AU2887884A (en)	1984-12-20
KR840009089A (ko)	1984-12-24
DE3461797D1 (en)	1987-02-05
CS405984A2 (en)	1985-09-17
FI77238B (fi)	1988-10-31
PH21555A (en)	1987-12-11
DK268484A (da)	1984-12-01
HU192405B (en)	1987-06-29
EP0127182B1 (en)	1986-12-30
YU92584A (cs)	1986-06-30
IE841346L (en)	1984-11-30
NO169895C (no)	1992-08-19
SU1355128A3 (ru)	1987-11-23
CA1215979A (en)	1986-12-30
EP0127182A1 (en)	1984-12-05
KR900001188B1 (ko)	1990-02-27
DK268484D0 (da)	1984-05-30
ES8505981A1 (es)	1985-06-16
IL71970A (en)	1988-02-29
DK163921C (da)	1992-09-21
PL247953A1 (en)	1985-03-26
FI842141A7 (fi)	1984-12-01
HUT34740A (en)	1985-04-28
IE57841B1 (en)	1993-04-21
PT78667A (en)	1984-06-01
YU43569B (en)	1989-08-31
NO169895B (no)	1992-05-11
ES532930A0 (es)	1985-06-16
NO842154L (no)	1984-12-03
CS245792B2 (en)	1986-10-16
JPS59227868A (ja)	1984-12-21
DK163921B (da)	1992-04-21
FI77238C (fi)	1989-02-10

Legal Events

Date	Code	Title	Description
2002-01-17	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
US3669968A (en)	1972-06-13	Trialkoxy quinazolines
DE68906834T2 (de)	1993-12-09	Pyrimidopyrimidinderivate.
EP0005828B1 (de)	1981-03-11	Neue substituierte Phenylpiperazinderivate, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung
EP0422485A2 (de)	1991-04-17	Chinoloncarbonsäurederivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als antivirale Mittel
EP0013894A1 (de)	1980-08-06	Neue Arylether, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE2164058B2 (de)	1980-10-23	Basisch substituierte Benzylphthalazinon-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und diese Produkte enthaltende pharmazeutische Präparate
CH643549A5 (de)	1984-06-15	N-(trimethoxybenzyl)-n'-phenylpiperazine.
EP0105210B1 (de)	1987-03-04	Isochinolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
EP0080176B1 (de)	1986-02-19	Triazolochinazoline, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
EP0122488B1 (de)	1989-06-07	Bis-(Piperazinyl- bzw. Homopiperazinyl)-Alkane
DD223710A5 (de)	1985-06-19	Verfahren zur herstellung von substituierten phenylalkyl (piperazinyl oder homopiperazinyl)-propyl-(harnstoffen oder thioharnstoffen).
DE3218792C2 (de)	1993-10-28	Isoprenylaminderivate und deren Säureadditionssalze, sowie diese enthaltende pharmazeutische Mittel
DE2040510C3 (de)	1980-03-06	Oxazole- und Thiazole eckige Klammer auf 5,4-d] azepin- Derivate
DE2502588A1 (de)	1976-07-29	Basisch substituierte derivate des 7-amino-2-chinolons, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3888215T2 (de)	1994-09-08	Piperazinylpyrimidine als beta-adrenergische Rezeptoren blockierende Mittel.
DE2231067A1 (de)	1973-01-18	Phenoxathiinderivate mit antiviraler wirkung, verfahren zu ihrer herstellung sowie pharmazeutische praeparate mit einem gehalt an phenoxathiinderivaten
EP0046506A1 (de)	1982-03-03	Vincamin-saccharinat und dieses enthaltende Arzneimittel
EP0064255A1 (de)	1982-11-10	Benzopyranylether, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel und Zwischenprodukte
DE2757532A1 (de)	1979-07-05	N,n'-disubstituiertes cyclisches diamin und verfahren zu dessen herstellung
EP0000334A1 (de)	1979-01-24	2,4--Diamino-5-benzylpyrimidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2445002C2 (de)	1984-11-22	N,N'-(Pyridin-diyl)-dioxamidsäurederivate und deren pharmazeutisch verträgliche Säureadditionssalze, Verfahren zu deren Herstellung und dieselben enthaltende pharmazeutische Mittel
EP0000336B1 (de)	1981-04-15	Amidino-benzylpyrimidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
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