NO880352L - Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider. - Google Patents

Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider.

Info

Publication number: NO880352L
Authority: NO; Norway
Prior art keywords: ethyl; piperazinecarboxamide; dimethylamino; mol; phenyl
Prior art date: 1987-01-28

Application number

NO880352A

Other languages

English (en)

Norwegian (no)

Other versions

NO880352D0 (no

Inventor

David Allan Walsh

Albert Duncan Cale Jr

Original Assignee

Robins Co Inc A H

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.)

1987-01-28

Filing date

1988-01-27

Publication date

1988-07-29

1988-01-27 Application filed by Robins Co Inc A H filed Critical Robins Co Inc A H

1988-01-27 Publication of NO880352D0 publication Critical patent/NO880352D0/no

1988-07-29 Publication of NO880352L publication Critical patent/NO880352L/no

Links

238000000034 method Methods 0.000 title claims description 62
-1 AMINO Chemical class 0.000 title claims description 40
238000002360 preparation method Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 136
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
150000002431 hydrogen Chemical group 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000012458 free base Substances 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
UXVMHPDFGRRXPH-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-nitrophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C([N+]([O-])=O)C=C1 UXVMHPDFGRRXPH-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
UAZPZIWLIHPPAJ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-[2-(dimethylamino)ethyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(Cl)C(Cl)=C1 UAZPZIWLIHPPAJ-UHFFFAOYSA-N 0.000 claims description 2
XMRJZABWSNOFGA-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-(dimethylamino)ethyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(Cl)C=C1 XMRJZABWSNOFGA-UHFFFAOYSA-N 0.000 claims description 2
NYZKRRCGNAMLNT-UHFFFAOYSA-N 4-phenyl-n-(2-pyrrolidin-1-ylethyl)piperazine-1-carboxamide Chemical compound C1CN(C=2C=CC=CC=2)CCN1C(=O)NCCN1CCCC1 NYZKRRCGNAMLNT-UHFFFAOYSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
150000001734 carboxylic acid salts Chemical class 0.000 claims description 2
HZBZEYXAHTVQKW-UHFFFAOYSA-N n-(1-ethylpiperidin-3-yl)-4-phenylpiperazine-1-carboxamide Chemical compound C1N(CC)CCCC1NC(=O)N1CCN(C=2C=CC=CC=2)CC1 HZBZEYXAHTVQKW-UHFFFAOYSA-N 0.000 claims description 2
KTUSITLQMUDEFW-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(2-methoxyphenyl)piperazine-1-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(C(=O)NCCN(C)C)CC1 KTUSITLQMUDEFW-UHFFFAOYSA-N 0.000 claims description 2
GOAJGCDPZXUQDR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-methoxyphenyl)piperazine-1-carboxamide Chemical compound COC1=CC=CC(N2CCN(CC2)C(=O)NCCN(C)C)=C1 GOAJGCDPZXUQDR-UHFFFAOYSA-N 0.000 claims description 2
YMWSDSKUNYUOKR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-fluorophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(F)C=C1 YMWSDSKUNYUOKR-UHFFFAOYSA-N 0.000 claims description 2
BGFQALRPQNDUKA-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-methoxyphenyl)piperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)NCCN(C)C)CC1 BGFQALRPQNDUKA-UHFFFAOYSA-N 0.000 claims description 2
XXYRQOAFNOQOER-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-methylphenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(C)C=C1 XXYRQOAFNOQOER-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
239000005864 Sulphur Chemical group 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 1
ZGSDJMADBJCNPN-UHFFFAOYSA-N [S-][NH3+] Chemical compound [S-][NH3+] ZGSDJMADBJCNPN-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 118
239000007787 solid Substances 0.000 description 93
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 59
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 56
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
239000000203 mixture Substances 0.000 description 52
238000004458 analytical method Methods 0.000 description 49
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 25
229910000041 hydrogen chloride Inorganic materials 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
241001465754 Metazoa Species 0.000 description 16
239000003208 petroleum Substances 0.000 description 16
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 14
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 13
235000011121 sodium hydroxide Nutrition 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000000047 product Substances 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000012360 testing method Methods 0.000 description 8
241000700159 Rattus Species 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000001665 trituration Methods 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
210000002683 foot Anatomy 0.000 description 6
239000008187 granular material Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
230000003266 anti-allergic effect Effects 0.000 description 5
239000000427 antigen Substances 0.000 description 5
102000036639 antigens Human genes 0.000 description 5
108091007433 antigens Proteins 0.000 description 5
239000012267 brine Substances 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
238000003756 stirring Methods 0.000 description 5
AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 4
241000700198 Cavia Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
208000026935 allergic disease Diseases 0.000 description 4
239000003054 catalyst 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
239000002904 solvent Substances 0.000 description 4
239000008174 sterile solution Substances 0.000 description 4
239000000829 suppository Substances 0.000 description 4
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 3
WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 3
HSTUDPLWWRFKDS-UHFFFAOYSA-N 4-piperazin-1-ylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1N1CCNCC1 HSTUDPLWWRFKDS-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
108010058846 Ovalbumin Proteins 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000036783 anaphylactic response Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
239000012153 distilled water Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000012216 screening Methods 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
IVTZRJKKXSKXKO-UHFFFAOYSA-N 1-(2-fluorophenyl)piperazine Chemical compound FC1=CC=CC=C1N1CCNCC1 IVTZRJKKXSKXKO-UHFFFAOYSA-N 0.000 description 2
QSTMOHFZTDLSBZ-UHFFFAOYSA-N 1-(3,4,5-trimethoxyphenyl)piperazine Chemical compound COC1=C(OC)C(OC)=CC(N2CCNCC2)=C1 QSTMOHFZTDLSBZ-UHFFFAOYSA-N 0.000 description 2
PXFJLKKZSWWVRX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)piperazine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCNCC1 PXFJLKKZSWWVRX-UHFFFAOYSA-N 0.000 description 2
VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 2
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
229940105325 3-dimethylaminopropylamine Drugs 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
DJJNYEXRPRQXPD-UHFFFAOYSA-N 4-piperazin-1-ylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1N1CCNCC1 DJJNYEXRPRQXPD-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
108010088751 Albumins Proteins 0.000 description 2
102000009027 Albumins Human genes 0.000 description 2
206010002198 Anaphylactic reaction Diseases 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
206010011224 Cough Diseases 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
206010030124 Oedema peripheral Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
230000007815 allergy Effects 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
208000003455 anaphylaxis Diseases 0.000 description 2
239000000043 antiallergic agent Substances 0.000 description 2
WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
230000028993 immune response Effects 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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SWGUDYFEQHUHOE-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(2-fluorophenyl)piperazine-1-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CN(C(=O)NCCN(C)C)CCN1C1=CC=CC=C1F SWGUDYFEQHUHOE-UHFFFAOYSA-N 0.000 description 1
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QKFMACQMXSIXNY-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-fluorophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=CC(F)=C1 QKFMACQMXSIXNY-UHFFFAOYSA-N 0.000 description 1
DZJOQCLDFPMFJK-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-phenylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=CC=C1 DZJOQCLDFPMFJK-UHFFFAOYSA-N 0.000 description 1
GTENIXUBDMTWFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-phenylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCCN(C)C)CCN1C1=CC=CC=C1 GTENIXUBDMTWFS-UHFFFAOYSA-N 0.000 description 1
RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000002663 nebulization Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical compound C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
210000003800 pharynx Anatomy 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
235000011118 potassium hydroxide Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
102220004588 rs104893797 Human genes 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000012353 t test Methods 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000009959 type I hypersensitivity Effects 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- C07D295/20—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 carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pulmonology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

NO880352A 1987-01-28 1988-01-27 Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider. NO880352L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/007,592 US4960776A (en)	1987-01-28	1987-01-28	4-aryl-N-(alkylaminoalkyl, heterocyclicamino and heterocyclicamino)alkyl)-1-piperazinecarboxamides

Publications (2)

Publication Number	Publication Date
NO880352D0 NO880352D0 (no)	1988-01-27
NO880352L true NO880352L (no)	1988-07-29

Family

ID=21727070

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO880352A NO880352L (no)	1987-01-28	1988-01-27	Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider.

Country Status (10)

Country	Link
US (1)	US4960776A (pt)
EP (1)	EP0277725A3 (pt)
JP (1)	JPS63188670A (pt)
AU (1)	AU8067687A (pt)
DK (1)	DK39988A (pt)
FI (1)	FI880371A (pt)
IL (1)	IL84045A0 (pt)
NO (1)	NO880352L (pt)
PT (1)	PT86635B (pt)
ZA (1)	ZA877371B (pt)

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* Cited by examiner, † Cited by third party
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JP3719612B2 (ja) *	1993-06-14	2005-11-24	塩野義製薬株式会社	ヘテロ環を含有する尿素誘導体
BR9605309A (pt) *	1995-01-11	1997-10-14	Samjin Pharmaceutical Co	Composições de derivados piperazina
US6211199B1 (en)	1995-11-17	2001-04-03	Aventis Pharmaceuticals Inc.	Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases
US6194406B1 (en)	1995-12-20	2001-02-27	Aventis Pharmaceuticals Inc.	Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease
US6423704B2 (en)	1995-12-20	2002-07-23	Aventis Pharmaceuticals Inc.	Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases
US5922737A (en) *	1996-02-21	1999-07-13	Hoechst Marion Roussel, Inc.	Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases
US5998439A (en) *	1996-02-21	1999-12-07	Hoescht Marion Roussel, Inc.	Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases
US5932571A (en) *	1996-02-21	1999-08-03	Hoechst Marion Roussel, Inc.	Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases
AU3565999A (en) *	1999-04-16	2000-11-02	Coelacanth Chemical Corporation	Synthesis of azetidine derivatives
GB0421908D0 (en)	2004-10-01	2004-11-03	Angeletti P Ist Richerche Bio	New uses
BRPI0708337A2 (pt) *	2006-02-28	2011-05-24	Helicon Therapeutics Inc	pipirazinas terapêutica como inibidores pde4
US8927546B2 (en)	2006-02-28	2015-01-06	Dart Neuroscience (Cayman) Ltd.	Therapeutic piperazines
FR2948370B1 (fr)	2009-07-27	2013-04-05	Sanofi Aventis	Derives d'uree de tetrahydroquinoxaline, leur preparation et leur application en therapeutique
FR2948369B1 (fr)	2009-07-27	2013-04-12	Sanofi Aventis	Derives d'uree de tetrahydroquinoxaline, leur preparation et leur application en therapeutique
US10689360B1 (en) *	2019-01-30	2020-06-23	Insilico Medicine Ip Limited	TLR inhibitors

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US2642255A (en) *	1947-12-10	1953-06-16	Weatherhead Co	Packless valve
US3133067A (en) *	1959-01-30	1964-05-12	Sterling Drug Inc	1-monocarbocyclic aryl-4-thiocarbam-ylpiperazines and intermediates and processes therefor
NO154582C (no) *	1978-10-20	1986-11-05	Ferrosan Ab	Analogifremgangsmaate for fremstilling av terapeutisk aktive difenyl-dibutylpiperazinkarboksamider.
JPS56127370A (en) *	1980-02-15	1981-10-06	Mitsui Toatsu Chem Inc	Novel piperazine compound, its preparation and utilization
US4593102A (en) *	1984-04-10	1986-06-03	A. H. Robins Company, Inc.	N-[(amino)alkyl]-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulfur linked substitution in the 2, 3 or 4-position
DE3420193A1 (de) *	1984-05-30	1985-12-05	Boehringer Ingelheim KG, 6507 Ingelheim	Neue substituierte pyrrolidinone, verfahren zu ihrer herstellung und arzneimittel
US4594343A (en) *	1984-10-19	1986-06-10	Shanklin Jr James R	1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-α,α-diarylpyrrolidine, piperidine and homopiperidineacetamides and acetonitriles

1987
- 1987-01-28 US US07/007,592 patent/US4960776A/en not_active Expired - Fee Related
- 1987-09-30 ZA ZA877371A patent/ZA877371B/xx unknown
- 1987-09-30 IL IL84045A patent/IL84045A0/xx unknown
- 1987-11-04 AU AU80676/87A patent/AU8067687A/en not_active Abandoned
- 1987-11-11 JP JP62285156A patent/JPS63188670A/ja active Pending
1988
- 1988-01-20 EP EP88300436A patent/EP0277725A3/en not_active Withdrawn
- 1988-01-27 PT PT86635A patent/PT86635B/pt not_active IP Right Cessation
- 1988-01-27 NO NO880352A patent/NO880352L/no unknown
- 1988-01-27 FI FI880371A patent/FI880371A/fi not_active IP Right Cessation
- 1988-01-27 DK DK039988A patent/DK39988A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK39988D0 (da)	1988-01-27
ZA877371B (en)	1988-04-11
US4960776A (en)	1990-10-02
NO880352D0 (no)	1988-01-27
AU8067687A (en)	1988-08-04
IL84045A0 (en)	1988-02-29
FI880371A (fi)	1988-07-29
PT86635A (pt)	1988-02-01
PT86635B (pt)	1992-01-31
EP0277725A2 (en)	1988-08-10
DK39988A (da)	1988-07-29
EP0277725A3 (en)	1988-08-31
FI880371A0 (fi)	1988-01-27
JPS63188670A (ja)	1988-08-04

Publication	Publication Date	Title
AU701420B2 (en)	1999-01-28	Novel piperazides derived from arylpiperazine, processes for their preparation, their use as medicaments and pharmaceutical compositions comprising them
NO880352L (no)	1988-07-29	Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider.
JP2941945B2 (ja)	1999-08-30	新規な４−アリールピペラジン類および４−アリールピペリジン類
KR100339460B1 (ko)	2002-09-18	씨씨알-3수용체길항제
US3813384A (en)	1974-05-28	Basically substituted benzyl phthalazone derivatives,acid salts thereof and process for the production thereof
AU750259B2 (en)	2002-07-11	Benzamide derivatives and their use as ApoB-100 secretion inhibitors
US20040242589A1 (en)	2004-12-02	3-arylsulfonyl-7-piperzinyl-indoles-benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders
CZ220399A3 (cs)	1999-11-17	Sulfonamidové deriváty, způsob jejich přípravy a jejich použití v léčivých prostředcích
BG64554B1 (bg)	2005-07-29	4-фенил-пиридинови производни, метод за получаването им и тяхното използване
US5569659A (en)	1996-10-29	4-arylpiperazines and 4-arylpiperidines
JP2006519812A (ja)	2006-08-31	フェニルスルホン誘導体およびｃｎｓ障害の治療におけるその使用
EP0462638A1 (en)	1991-12-27	Pyridinylpiperazine derivatives
JPH0723365B2 (ja)	1995-03-15	フエノキシアルキルまたはチオフエノキシアルキル側鎖を有する新規ピペラジンカルボキシアミド化合物
NO174667B (no)	1994-03-07	Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyridyl- og pyrimidylderivater
US4247549A (en)	1981-01-27	Piperazine-1-carboxylic acid esters possessing antidepressant or analgesic activity
EP0147909B1 (en)	1989-12-06	Aryloxy-n-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides having antiarrhythmic activity
KR20030024919A (ko)	2003-03-26	Ｎ-(3,5-디클로로-2-메톡시페닐)-4-메톡시-3-피페라진-1-일-벤젠술폰아미드
US5086055A (en)	1992-02-04	Series of 5-[-(4-aryl-1-piperazinyl)alkyl]-2-oxazolidinone derivatives useful in the treatment of allergic conditions
CS241064B2 (en)	1986-03-13	Method of n-substituted nicotinamide's 1-oxide and its salts production
CA2139112C (en)	2006-03-21	Novel nicotinic acid esters
EP0269383A2 (en)	1988-06-01	1-Aryloxy-4-[(4-aryl)-1-piperazinyl]-2-butanols useful as antiallergy agents
JPH01113377A (ja)	1989-05-02	ピペラジン化合物
DK163921B (da)	1992-04-21	Substituerede (piperazinyl eller homopiperazinyl)alkylthioler og -thiocarbamater og salte deraf, fremgangsmaade til deres fremstilling og immunologisk, antiallergisk eller antiinflammatorisk praeparat indeholdende dem
DE19940829A1 (de)	2001-03-01	Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel
EP0291244A1 (en)	1988-11-17	Cyclic carbamate derivatives