DK167187B1 - 1,4-disubstituerede piperaziner og syreadditionssalte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt en fremgangsmaade til fremstilling af forbindelserne - Google Patents

1,4-disubstituerede piperaziner og syreadditionssalte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt en fremgangsmaade til fremstilling af forbindelserne Download PDF

Info

Publication number: DK167187B1
Authority: DK; Denmark
Prior art keywords: formula; compound; piperazine; compounds; salt
Prior art date: 1986-06-16

Application number

DK303387A

Other languages

Danish (da)

English (en)

Other versions

DK303387D0 (da

DK303387A (da

Inventor

Pier Giorgio Ferrini

Andreas Von Sprecher

Original Assignee

Ciba Geigy 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.)

1986-06-16

Filing date

1987-06-15

Publication date

1993-09-13

1987-06-15 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1987-06-15 Publication of DK303387D0 publication Critical patent/DK303387D0/da

1987-12-17 Publication of DK303387A publication Critical patent/DK303387A/da

1993-09-13 Application granted granted Critical

1993-09-13 Publication of DK167187B1 publication Critical patent/DK167187B1/da

Links

150000003839 salts Chemical class 0.000 title claims abstract description 75
150000001875 compounds Chemical class 0.000 title claims description 118
238000000034 method Methods 0.000 title claims description 61
239000002253 acid Chemical class 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 18
150000004885 piperazines Chemical class 0.000 title abstract 2
239000000825 pharmaceutical preparation Substances 0.000 title description 3
-1 C1-C7-alkoxy Chemical group 0.000 claims abstract description 86
229910052736 halogen Inorganic materials 0.000 claims abstract description 31
150000002367 halogens Chemical group 0.000 claims abstract description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 35
230000008569 process Effects 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
239000000460 chlorine Substances 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 12
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
YPLSFHBFZLTZQF-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical group COC1=CC(OC)=CC(C(=O)N2CCN(CCC=3C=CC(Cl)=CC=3)CC2)=C1 YPLSFHBFZLTZQF-UHFFFAOYSA-N 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims 1
125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
239000004480 active ingredient Substances 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
235000002639 sodium chloride Nutrition 0.000 description 62
239000000243 solution Substances 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
GMIRFHIMHXOTKR-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1CCN1CCNCC1 GMIRFHIMHXOTKR-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
239000007858 starting material Substances 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000002585 base Substances 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
229940086542 triethylamine Drugs 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000000202 analgesic effect Effects 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000000725 suspension Substances 0.000 description 8
229920002472 Starch Polymers 0.000 description 7
239000000155 melt Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
229920001223 polyethylene glycol Polymers 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
150000001718 carbodiimides Chemical class 0.000 description 5
238000000576 coating method Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
238000007126 N-alkylation reaction Methods 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
239000013078 crystal Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
229940014259 gelatin Drugs 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000829 suppository Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
LKUAPSRIYZLAAO-UHFFFAOYSA-N 1-(2-phenylethyl)piperazine Chemical compound C1CNCCN1CCC1=CC=CC=C1 LKUAPSRIYZLAAO-UHFFFAOYSA-N 0.000 description 3
CLKQGHYYLMDFID-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)ethyl]piperazine Chemical compound ClC1=CC=CC(CCN2CCNCC2)=C1 CLKQGHYYLMDFID-UHFFFAOYSA-N 0.000 description 3
LODHVDKKTUZVDK-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]piperazine Chemical compound C1=CC(F)=CC=C1CCN1CCNCC1 LODHVDKKTUZVDK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
150000003973 alkyl amines Chemical class 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000009835 boiling Methods 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
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
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230000003389 potentiating effect Effects 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FLRUNCJXOVYWDH-UHFFFAOYSA-N 1-(2-bromoethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCBr)C=C1 FLRUNCJXOVYWDH-UHFFFAOYSA-N 0.000 description 2
AQFXIWDRLHRFIC-UHFFFAOYSA-N 1-[5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound CC(=O)N1N=C(C(F)(F)F)C=C1C1=CC=CC=C1 AQFXIWDRLHRFIC-UHFFFAOYSA-N 0.000 description 2
MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 2
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 2
QBTDQJMLMVEUTQ-UHFFFAOYSA-N 3,5-diacetyloxybenzoic acid Chemical compound CC(=O)OC1=CC(OC(C)=O)=CC(C(O)=O)=C1 QBTDQJMLMVEUTQ-UHFFFAOYSA-N 0.000 description 2
UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
IWPZKOJSYQZABD-UHFFFAOYSA-N 3,5-dimethoxybenzoic acid Chemical compound COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 2
FTHPLWDYWAKYCY-UHFFFAOYSA-N 3,5-dimethoxybenzoyl chloride Chemical compound COC1=CC(OC)=CC(C(Cl)=O)=C1 FTHPLWDYWAKYCY-UHFFFAOYSA-N 0.000 description 2
NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
238000009619 Gattermann reaction Methods 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000000297 Sandmeyer reaction Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
FGJPXHHDBTTZBF-UHFFFAOYSA-N [4-(1-phenylethyl)piperazin-1-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CCN(CC2)C(C)C=2C=CC=CC=2)=C1 FGJPXHHDBTTZBF-UHFFFAOYSA-N 0.000 description 2
IBJGXBBHOCQEJU-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC(C(=O)N2CCN(CCC=3C=CC(Cl)=CC=3)CC2)=C1 IBJGXBBHOCQEJU-UHFFFAOYSA-N 0.000 description 2
ITRWZFVGJDQZIU-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2CCN(CCC=3C=CC(Cl)=CC=3)CC2)=C1 ITRWZFVGJDQZIU-UHFFFAOYSA-N 0.000 description 2
CJZHOJARNOFKGY-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCN(CCC=2C=CC(Cl)=CC=2)CC1 CJZHOJARNOFKGY-UHFFFAOYSA-N 0.000 description 2
SZFKPJVKDMGYOG-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)N2CCN(CCC=3C=CC(Cl)=CC=3)CC2)=C1 SZFKPJVKDMGYOG-UHFFFAOYSA-N 0.000 description 2
XTQLJIHMIOXTMS-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1CCN(CCC=2C=CC(Cl)=CC=2)CC1 XTQLJIHMIOXTMS-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
150000008051 alkyl sulfates Chemical class 0.000 description 2
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230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc 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
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/18—Oxygen or sulfur atoms
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- 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
- C07D295/06—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 halogen atoms or nitro radicals
- C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- 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
- C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Pain & Pain Management (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Lubricants (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Water Treatment By Sorption (AREA)
Removal Of Specific Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK303387A 1986-06-16 1987-06-15 1,4-disubstituerede piperaziner og syreadditionssalte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt en fremgangsmaade til fremstilling af forbindelserne DK167187B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH242086		1986-06-16
CH242086		1986-06-16

Publications (3)

Publication Number	Publication Date
DK303387D0 DK303387D0 (da)	1987-06-15
DK303387A DK303387A (da)	1987-12-17
DK167187B1 true DK167187B1 (da)	1993-09-13

Family

ID=4233392

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK303387A DK167187B1 (da)	1986-06-16	1987-06-15	1,4-disubstituerede piperaziner og syreadditionssalte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt en fremgangsmaade til fremstilling af forbindelserne

Country Status (20)

Country	Link
US (1)	US4804661A (xx)
EP (1)	EP0250361B1 (xx)
JP (1)	JPS62298580A (xx)
KR (1)	KR880000410A (xx)
AT (1)	ATE98237T1 (xx)
AU (1)	AU603584B2 (xx)
DD (1)	DD263289A5 (xx)
DE (1)	DE3788373D1 (xx)
DK (1)	DK167187B1 (xx)
ES (1)	ES2060607T3 (xx)
FI (1)	FI86545C (xx)
HU (1)	HU202508B (xx)
IE (1)	IE61477B1 (xx)
IL (1)	IL82817A0 (xx)
MX (1)	MX6924A (xx)
MY (1)	MY102447A (xx)
NO (1)	NO169961C (xx)
PH (1)	PH23350A (xx)
PT (1)	PT85079B (xx)
ZA (1)	ZA874278B (xx)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR910006138B1 (ko) *	1986-09-30	1991-08-16	에자이 가부시끼가이샤	환상아민 유도체
IL85700A0 (en) *	1987-03-24	1988-08-31	Takeda Chemical Industries Ltd	1,4-disubstituted piperazine compounds,their production and use
EP0385043A1 (en) *	1989-02-28	1990-09-05	Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes)	New derivatives of 4-substituted piperazines
EP0489690A1 (de) *	1990-12-05	1992-06-10	Ciba-Geigy Ag	Substituierte N-Benzoyl-N'-(2-phenylethyl)-piperazine
EP0524146A1 (de) *	1991-07-19	1993-01-20	Ciba-Geigy Ag	Aminosubstituierte Piperazinderivate
US5387595A (en) *	1992-08-26	1995-02-07	Merck & Co., Inc.	Alicyclic compounds as tachykinin receptor antagonists
US5344830A (en) *	1992-12-10	1994-09-06	Merck & Co., Inc.	N,N-diacylpiperazine tachykinin antagonists
US5384319A (en) *	1993-01-06	1995-01-24	Ciba-Geigy Corporation	Aminoalkylphenyl compounds
US5380726A (en) *	1993-01-15	1995-01-10	Ciba-Geigy Corporation	Substituted dialkylthio ethers
US5610165A (en) *	1994-02-17	1997-03-11	Merck & Co., Inc.	N-acylpiperidine tachykinin antagonists
JP6486198B2 (ja) *	2015-05-27	2019-03-20	国立大学法人宮崎大学	アンチモンイオンの抽出剤及びアンチモンイオンの回収方法
WO2023117119A1 (de) *	2021-12-23	2023-06-29	Symrise Ag	Wirkstoffe mit mundwässerndem und kribbelndem/prickelndem effekt und zubereitungen, die diese enthalten

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL105768C (xx) *	1959-02-25
US3000892A (en) *	1959-11-16	1961-09-19	Paul A J Janssen	1-aroylalkyl-4-aroylpiperazines
FR7170M (xx) *	1966-12-28	1969-08-11
CH590261A5 (xx) *	1973-07-10	1977-07-29	Ciba Geigy Ag
US3917617A (en) *	1973-10-01	1975-11-04	Sharps Ass	1-{8 2,6-Dihydroxy-4-hydrocarbyl-benzoyl{9 polymethyleneimines and derivatives
JPS50151885A (xx) *	1974-05-29	1975-12-06
EP0008072B1 (de) *	1978-08-10	1984-02-22	Ciba-Geigy Ag	Substituierte Anthranilsäureamide, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate und ihre Herstellung
WO1981003658A1 (en) *	1980-06-16	1981-12-24	Ferrosan Ab	Diphenylbutyl-1-acylpiperazines
FR2522325B1 (fr) *	1982-02-26	1985-08-09	Delalande Sa	Nouveaux derives aryliques de la piperazine, de l'homopiperazine et de n,n'-dialkyl diamino-1,2 ethane, leur procede de preparation et leur application en therapeutique
AU545463B2 (en) *	1982-06-25	1985-07-18	Kowa Co. Ltd.	Benzoyl piperacine esters
IT1176613B (it) *	1984-08-14	1987-08-18	Ravizza Spa	Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione
KR910006138B1 (ko) *	1986-09-30	1991-08-16	에자이 가부시끼가이샤	환상아민 유도체
IL85700A0 (en) *	1987-03-24	1988-08-31	Takeda Chemical Industries Ltd	1,4-disubstituted piperazine compounds,their production and use

1987
- 1987-05-26 MY MYPI87000720A patent/MY102447A/en unknown
- 1987-06-09 IL IL82817A patent/IL82817A0/xx not_active IP Right Cessation
- 1987-06-09 US US07/059,898 patent/US4804661A/en not_active Expired - Fee Related
- 1987-06-10 ES ES87810331T patent/ES2060607T3/es not_active Expired - Lifetime
- 1987-06-10 EP EP87810331A patent/EP0250361B1/de not_active Expired - Lifetime
- 1987-06-10 AT AT87810331T patent/ATE98237T1/de not_active IP Right Cessation
- 1987-06-10 DE DE87810331T patent/DE3788373D1/de not_active Expired - Fee Related
- 1987-06-12 FI FI872637A patent/FI86545C/fi not_active IP Right Cessation
- 1987-06-12 MX MX692487A patent/MX6924A/es unknown
- 1987-06-15 AU AU74219/87A patent/AU603584B2/en not_active Ceased
- 1987-06-15 HU HU872710A patent/HU202508B/hu not_active IP Right Cessation
- 1987-06-15 KR KR1019870006034A patent/KR880000410A/ko not_active Ceased
- 1987-06-15 NO NO872480A patent/NO169961C/no unknown
- 1987-06-15 ZA ZA874278A patent/ZA874278B/xx unknown
- 1987-06-15 DD DD87303827A patent/DD263289A5/de not_active IP Right Cessation
- 1987-06-15 DK DK303387A patent/DK167187B1/da not_active Application Discontinuation
- 1987-06-15 JP JP62147163A patent/JPS62298580A/ja active Granted
- 1987-06-15 IE IE158287A patent/IE61477B1/en not_active IP Right Cessation
- 1987-06-15 PH PH35398A patent/PH23350A/en unknown
- 1987-06-15 PT PT85079A patent/PT85079B/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
DD263289A5 (de)	1988-12-28
FI86545C (fi)	1992-09-10
AU603584B2 (en)	1990-11-22
EP0250361A2 (de)	1987-12-23
ATE98237T1 (de)	1993-12-15
DK303387D0 (da)	1987-06-15
FI872637A0 (fi)	1987-06-12
ZA874278B (en)	1987-12-15
MY102447A (en)	1992-06-30
KR880000410A (ko)	1988-03-25
HU202508B (en)	1991-03-28
FI86545B (fi)	1992-05-29
MX6924A (es)	1993-12-01
IE871582L (en)	1987-12-16
EP0250361A3 (en)	1990-01-31
US4804661A (en)	1989-02-14
EP0250361B1 (de)	1993-12-08
ES2060607T3 (es)	1994-12-01
NO169961B (no)	1992-05-18
PT85079B (pt)	1990-03-08
IE61477B1 (en)	1994-11-02
NO169961C (no)	1992-08-26
JPS62298580A (ja)	1987-12-25
AU7421987A (en)	1987-12-17
NO872480L (no)	1987-12-17
PH23350A (en)	1989-07-14
HUT44529A (en)	1988-03-28
DE3788373D1 (de)	1994-01-20
IL82817A0 (en)	1987-12-20
NO872480D0 (no)	1987-06-15
FI872637L (fi)	1987-12-17
DK303387A (da)	1987-12-17
PT85079A (en)	1987-07-01
JPH0579065B2 (xx)	1993-11-01

Publication	Publication Date	Title
AU667107B2 (en)	1996-03-07	Thiazolylvinylphenyl derivatives
EP0076072B1 (en)	1987-05-13	Sulphonamides
DK167187B1 (da)	1993-09-13	1,4-disubstituerede piperaziner og syreadditionssalte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt en fremgangsmaade til fremstilling af forbindelserne
NO155805B (no)	1987-02-23	Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter.
NO162965B (no)	1989-12-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive alfa-(2-okso-2,4,5,6,7,7a-heksahydrotieno-(3,2-c)-5-pyridyl)-fenyl-eddiksyre-derivater.
CA1140564A (en)	1983-02-01	Benzoyl derivatives, their preparation and their use as pharmaceutical compositions
CS228910B2 (en)	1984-05-14	Method of preparing new substituted alkyleneiminophenylalkyl amides of phenylalkane carboxylic acids
SU1195903A3 (ru)	1985-11-30	Способ получени 1-фенил- 2-аминокарбонилиндольных соединений или их солей присоединени кислот
US4882329A (en)	1989-11-21	Alkoxyphenylindolinone derivatives, medicaments containing them and their use
EP1289971A1 (en)	2003-03-12	Benzamide derivatives and their use as apob-100 and mtp inhibitors
US4767769A (en)	1988-08-30	Antiulcer benzimidazole derivatives
CS236668B2 (en)	1985-05-15	Manufacturing process of aralkylamides 2-substituted aminophenylalkancarboxyle and amino-3-pyridylalkancarboxyl acides
US4515944A (en)	1985-05-07	1,5-Diphenyl-2-haloalkylpyrazolin-3-one intermediates
WO2002036564A1 (de)	2002-05-10	Sulfonylamino substituierte 3-(aminomethyliden)-2-indolinone als inhibitoren der zellproliferation
US4603130A (en)	1986-07-29	1-substituted-2-(piperazinyl or homopiperazinyl)-benzimidazole compounds and pharmaceutical composition
US4505913A (en)	1985-03-19	Substituted anthranilamides and pharmaceutical preparations containing these compounds
PL179032B1 (pl)	2000-07-31	kwasu hydroksamowego oraz kompozycje farmaceutyczne zawierajace nowe pochodnekwasu hydroksamowego PL PL
US4448777A (en)	1984-05-15	1-Phenylindazole-3-one compounds, process and intermediates for their preparation, and pharmaceutical compositions containing same
CS248720B2 (en)	1987-02-12	Production method of quinolines
DK166022B (da)	1993-03-01	Bis-(piperazinyl- eller homopiperazinyl)-alkaner og syreadditionssalte deraf, fremgangsmaade til deres fremstilling, farmaceutiske praeparater indeholdende forbindelserne, fremgangsmaade til fremstilling af saadanne praeparater og anvendelse af forbindelserne til fremstilling af et farmaceutisk praeparat med antiallergisk og antiinflammatorisk virkning
EP0489690A1 (de)	1992-06-10	Substituierte N-Benzoyl-N'-(2-phenylethyl)-piperazine
CS241064B2 (en)	1986-03-13	Method of n-substituted nicotinamide's 1-oxide and its salts production
EP0168003A1 (en)	1986-01-15	Oxindol compounds, compositions containing same and processes for preparing same
US3758483A (en)	1973-09-11	Tetrahydropyridine derivatives
CA1281328C (en)	1991-03-12	Disubstituted piperazines

Legal Events

Date	Code	Title	Description
1993-05-24	AHB	Application shelved due to non-payment