CA1051888A - Composes de piperazinyl-pyridine - Google Patents

Composes de piperazinyl-pyridine

Info

Publication number: CA1051888A
Authority: CA; Canada
Prior art keywords: group; formula; piperazinyl; compound; methyl
Prior art date: 1974-04-04
Legal status (The legal status 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 status listed.): Expired

Application number

CA223,696A

Other languages

English (en)

Other versions

CA223696S (en

Inventor

Charles L. Lapiere

Andre H. Georges

Jacques E. Delarge

Leopold N. Thunus

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

A Christiaens SA

Original Assignee

A Christiaens SA

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.)

1974-04-04

Filing date

1975-04-02

Publication date

1979-04-03

1975-04-02 Application filed by A Christiaens SA filed Critical A Christiaens SA

1979-04-03 Application granted granted Critical

1979-04-03 Publication of CA1051888A publication Critical patent/CA1051888A/fr

Status Expired legal-status Critical Current

Links

GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical class C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 title 1
-1 methylpiperazinyl group Chemical group 0.000 claims abstract description 21
150000003222 pyridines Chemical class 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 49
238000000034 method Methods 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 6
HMSYOMRFLOKYEK-UHFFFAOYSA-N 1-pyrrolidin-1-ylsulfonylpyrrolidine Chemical compound C1CCCN1S(=O)(=O)N1CCCC1 HMSYOMRFLOKYEK-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
ZVGYRRQWDXORHY-UHFFFAOYSA-N 1-piperidin-1-ylsulfonylpiperidine Chemical compound C1CCCCN1S(=O)(=O)N1CCCCC1 ZVGYRRQWDXORHY-UHFFFAOYSA-N 0.000 claims description 4
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 3
SOBXUYMZUBUAOG-UHFFFAOYSA-N 4-morpholin-4-ylsulfonylmorpholine Chemical compound C1COCCN1S(=O)(=O)N1CCOCC1 SOBXUYMZUBUAOG-UHFFFAOYSA-N 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 4
JJWOMLRJNXMLSO-UHFFFAOYSA-N 1-methylsulfonylpiperidine Chemical compound CS(=O)(=O)N1CCCCC1 JJWOMLRJNXMLSO-UHFFFAOYSA-N 0.000 claims 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
230000002526 effect on cardiovascular system Effects 0.000 abstract description 4
230000001754 anti-pyretic effect Effects 0.000 abstract description 2
239000002221 antipyretic Substances 0.000 abstract description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 abstract 1
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
125000002757 morpholinyl group Chemical group 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
125000005936 piperidyl group Chemical group 0.000 abstract 1
125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 14
239000000243 solution Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000004193 piperazinyl group Chemical group 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
241000700159 Rattus Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000008298 dragée Substances 0.000 description 3
210000002683 foot Anatomy 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
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 2
235000019759 Maize starch Nutrition 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
239000008119 colloidal silica Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
238000007429 general method Methods 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000008101 lactose Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000012360 testing method Methods 0.000 description 2
230000002861 ventricular Effects 0.000 description 2
AZRCSTMIVMQIPR-UHFFFAOYSA-N 4-oxo-1h-pyridine-3-sulfonic acid Chemical compound OC1=CC=[NH+]C=C1S([O-])(=O)=O AZRCSTMIVMQIPR-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
102100038916 Caspase-5 Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
206010047141 Vasodilatation Diseases 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007775 late Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LMINNBXUMGNKMM-UHFFFAOYSA-N metiazinic acid Chemical compound C1=C(CC(O)=O)C=C2N(C)C3=CC=CC=C3SC2=C1 LMINNBXUMGNKMM-UHFFFAOYSA-N 0.000 description 1
229950005798 metiazinic acid Drugs 0.000 description 1
229940048276 new coccine Drugs 0.000 description 1
229960000916 niflumic acid Drugs 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
239000003883 ointment base Substances 0.000 description 1
WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
229960002195 perazine Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
235000012731 ponceau 4R Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000000541 pulsatile effect Effects 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
235000012756 tartrazine Nutrition 0.000 description 1
229960000943 tartrazine Drugs 0.000 description 1
239000004149 tartrazine Substances 0.000 description 1
SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

CA223,696A 1974-04-04 1975-04-02 Composes de piperazinyl-pyridine Expired CA1051888A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1509474		1974-04-04

Publications (1)

Publication Number	Publication Date
CA1051888A true CA1051888A (fr)	1979-04-03

Family

ID=10052924

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA223,696A Expired CA1051888A (fr)	1974-04-04	1975-04-02	Composes de piperazinyl-pyridine

Country Status (8)

Country	Link
JP (1)	JPS50140469A (fr)
BE (1)	BE827326A (fr)
CA (1)	CA1051888A (fr)
DE (1)	DE2514334A1 (fr)
ES (1)	ES436109A1 (fr)
FR (1)	FR2266506A1 (fr)
LU (1)	LU72195A1 (fr)
NL (1)	NL7503975A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6635765B2 (en)	2000-03-20	2003-10-21	Teva Pharmaceutical Industries, Ltd.	Processes for preparing torsemide intermediate
US7423147B2 (en)	2004-03-31	2008-09-09	Janssen Pharmaceutical, N.V.	Pyridine compounds as histamine H3 modulators
US7777031B2 (en)	2006-05-30	2010-08-17	Janssen Pharmaceutica Nv	Substituted pyridyl amide compounds as modulators of the histamine H3 receptor
US8883776B2 (en)	2007-11-20	2014-11-11	Janssen Pharmaceutica N.V.	Cycloalkyloxy- and heterocycloalkyloxypyridine compounds as modulators of the histamine H3 receptor

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4994456A (en) *	1989-03-01	1991-02-19	Nisshin Flour Milling Co., Ltd.	Pyridinecarboxylic acid amide derivatives and pharmaceutical compositions comprising same
DE19918021C1 (de) *	1999-04-21	2000-06-29	Ruetgers Organics Gmbh	Verfahren zur Herstellung von chlorierten Pyridinsulfonsäurechloriden
WO2005118543A1 (fr) *	2004-06-03	2005-12-15	Ono Pharmaceutical Co., Ltd.	Inhibiteur des kinases et utilisation de cet inhibiteur
JP2007031391A (ja) *	2005-07-29	2007-02-08	Koei Chem Co Ltd	アルキルアミノピリジンカルボニトリルの製造方法

1975
- 1975-03-27 ES ES436109A patent/ES436109A1/es not_active Expired
- 1975-03-28 BE BE154892A patent/BE827326A/fr unknown
- 1975-04-02 FR FR7510222A patent/FR2266506A1/fr not_active Withdrawn
- 1975-04-02 CA CA223,696A patent/CA1051888A/fr not_active Expired
- 1975-04-02 DE DE19752514334 patent/DE2514334A1/de not_active Withdrawn
- 1975-04-02 LU LU72195A patent/LU72195A1/xx unknown
- 1975-04-03 NL NL7503975A patent/NL7503975A/xx not_active Application Discontinuation
- 1975-04-04 JP JP4175475A patent/JPS50140469A/ja active Pending

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6635765B2 (en)	2000-03-20	2003-10-21	Teva Pharmaceutical Industries, Ltd.	Processes for preparing torsemide intermediate
US6670478B2 (en)	2000-03-20	2003-12-30	Teva Pharmaceutical Industries, Ltd.	Process for preparing torsemide intermediate
US7423147B2 (en)	2004-03-31	2008-09-09	Janssen Pharmaceutical, N.V.	Pyridine compounds as histamine H3 modulators
US7947718B2 (en)	2004-03-31	2011-05-24	Janssen Pharmaceutica Nv	Isoxazole compounds as histamine H3 modulators
US7777031B2 (en)	2006-05-30	2010-08-17	Janssen Pharmaceutica Nv	Substituted pyridyl amide compounds as modulators of the histamine H3 receptor
US8637520B2 (en)	2006-05-30	2014-01-28	Janssen Pharmaceutica Nv	Substituted pyridyl amide compounds as modulators of the histamine H3 receptor
US8940731B2 (en)	2006-05-30	2015-01-27	Janssen Pharmaceutica Nv	Substituted pyridyl amide compounds as modulators of the histamine H3 receptor
US9321729B2 (en)	2006-05-30	2016-04-26	Janssen Pharmaceutica Nv	Substituted pyridyl amide compounds as modulators of the histamine H3 receptor
US8883776B2 (en)	2007-11-20	2014-11-11	Janssen Pharmaceutica N.V.	Cycloalkyloxy- and heterocycloalkyloxypyridine compounds as modulators of the histamine H3 receptor

Also Published As

Publication number	Publication date
JPS50140469A (ja)	1975-11-11
DE2514334A1 (de)	1975-10-09
BE827326A (fr)	1975-09-29
FR2266506A1 (en)	1975-10-31
LU72195A1 (fr)	1975-08-20
NL7503975A (nl)	1975-10-07
ES436109A1 (es)	1977-01-01

Publication	Publication Date	Title
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PL92131B1 (fr)	1977-03-31
US4330542A (en)	1982-05-18	N(Sulfonyl)anilines for treating angina pectoris
CA1168232A (fr)	1984-05-29	Derives de l'isoquinoline, methode de preparation, compositions pharmaceutiques les renfermant et usages
PL117515B1 (en)	1981-08-31	Process for preparing novel,substituted aminothiazoles
CA1051888A (fr)	1979-04-03	Composes de piperazinyl-pyridine
Klayman et al.	1984	2-Acetylpyridine thiosemicarbazones. 8. Derivatives of 1-acetylisoquinoline as potential antimalarial agents
DK164907B (da)	1992-09-07	Piperazinderivater, deres fremstilling og farmaceutiske praeparater indeholdende dem
US3810896A (en)	1974-05-14	Flavonyloxyalkyl-piperazine compounds
US4315940A (en)	1982-02-16	Antidiabetic 1-piperidine-sulfonylureas
ES8601934A1 (es)	1985-04-16	Un procedimiento para la preparacion de nuevos derivados de triazina.
US3330831A (en)	1967-07-11	Aminoalkoxy-diphenyl amines, ethers and thioethers
DE2702600A1 (de)	1978-07-27	Neue aminoalkoxyphenyl-derivate
US4397855A (en)	1983-08-09	4-(Substituted)-α, α-dimethyl-1-piperazine pentanoic acids and derivatives as anti-arteriosclerotic agents and method
DE3248957T1 (de)	1983-10-20	Benzothiazolinverbindungen
EP0138198B1 (fr)	1991-01-02	Dérivés diurétiques d'isoindoles
DE3375917D1 (en)	1988-04-14	Thiomethylpyridine derivatives, process for their preparation and medicaments containing them
US4665173A (en)	1987-05-12	2-acetyl- and 2-propionylpyridine selenosemicarbazones
US4335123A (en)	1982-06-15	1-Acyl-8-(3-amino-2-hydroxypropoxy)-1,2,3,4-tetrahydroquinolines, compositions and use
NO127149B (fr)	1973-05-14
US4542139A (en)	1985-09-17	Sulfonylureas pharmaceutical formulations based on these compounds and their use for treatment of diabetes
DE3626554A1 (de)	1988-02-18	Diselenobis-benzoesaeureamide primaerer heterocyclischer amine, verfahren zur ihrer herstellung und diese enthaltende pharmazeutische praeparate
US3007935A (en)	1961-11-07	Certificate of correction
GB1582239A (en)	1981-01-07	Piperidin-4-yl ureas and thioureas
US4014884A (en)	1977-03-29	Basically substituted 3,4-dihydro-2H-isoquinolin-1-thiones