HU195509B - Process for producing pyridinyl-piperazine derivatives and pharmaceutical compositions containing them as active agents - Google Patents

Process for producing pyridinyl-piperazine derivatives and pharmaceutical compositions containing them as active agents Download PDF

Info

Publication number: HU195509B
Authority: HU; Hungary
Prior art keywords: formula; compounds; compound; acid; alkyl
Prior art date: 1985-05-06

Application number

HU861860A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT43848A (en

Inventor

James S New

P Joseph Yevich

Original Assignee

Bristol Myers Co

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.)

1985-05-06

Filing date

1986-05-06

Publication date

1988-05-30

1986-05-06 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1987-12-28 Publication of HUT43848A publication Critical patent/HUT43848A/hu

1988-05-30 Publication of HU195509B publication Critical patent/HU195509B/hu

Links

238000000034 method Methods 0.000 title claims description 18
239000008194 pharmaceutical composition Substances 0.000 title claims description 12
230000008569 process Effects 0.000 title claims description 5
GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical class C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 title description 2
239000013543 active substance Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 112
239000002253 acid Substances 0.000 claims description 17
230000000694 effects Effects 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 15
-1 1,4-butylene Chemical group 0.000 claims description 14
230000000561 anti-psychotic effect Effects 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims 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 claims description 3
150000008051 alkyl sulfates Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
239000005557 antagonist Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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208000009132 Catalepsy Diseases 0.000 description 11
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239000000203 mixture Substances 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
230000000701 neuroleptic effect Effects 0.000 description 9
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IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
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238000001727 in vivo Methods 0.000 description 7
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239000007787 solid Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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239000004480 active ingredient Substances 0.000 description 6
239000000164 antipsychotic agent Substances 0.000 description 6
230000027455 binding Effects 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
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NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
229940005529 antipsychotics Drugs 0.000 description 4
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 4
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210000003169 central nervous system Anatomy 0.000 description 4
QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 4
229960004170 clozapine Drugs 0.000 description 4
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VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
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230000005764 inhibitory process Effects 0.000 description 4
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238000007911 parenteral administration Methods 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000000746 purification Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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102000005962 receptors Human genes 0.000 description 4
238000010992 reflux Methods 0.000 description 4
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
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208000027776 Extrapyramidal disease Diseases 0.000 description 3
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230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
238000003556 assay Methods 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
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239000003937 drug carrier Substances 0.000 description 3
125000005462 imide group Chemical group 0.000 description 3
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125000004193 piperazinyl group Chemical group 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
230000002441 reversible effect Effects 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical group C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 3
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical group C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 2
KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 2
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CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
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239000012458 free base Substances 0.000 description 1
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235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
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239000000314 lubricant Substances 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
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238000012986 modification Methods 0.000 description 1
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235000005985 organic acids Nutrition 0.000 description 1
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235000010603 pastilles Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
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229960001999 phentolamine Drugs 0.000 description 1
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UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
CNMOHEDUVVUVPP-UHFFFAOYSA-N piperidine-2,3-dione Chemical group O=C1CCCNC1=O CNMOHEDUVVUVPP-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
108010092215 spiroperidol receptor Proteins 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 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
238000012360 testing method Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
150000001467 thiazolidinediones Chemical class 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
229960002324 trifluoperazine Drugs 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- 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
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

HU861860A 1985-05-06 1986-05-06 Process for producing pyridinyl-piperazine derivatives and pharmaceutical compositions containing them as active agents HU195509B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US73120185A	1985-05-06	1985-05-06

Publications (2)

Publication Number	Publication Date
HUT43848A HUT43848A (en)	1987-12-28
HU195509B true HU195509B (en)	1988-05-30

Family

ID=24938510

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU861860A HU195509B (en)	1985-05-06	1986-05-06	Process for producing pyridinyl-piperazine derivatives and pharmaceutical compositions containing them as active agents

Country Status (25)

Country	Link
JP (1)	JPH0753728B2 (xx)
KR (1)	KR940000829B1 (xx)
CN (1)	CN1017901B (xx)
AT (1)	AT398572B (xx)
AU (1)	AU593244B2 (xx)
BE (1)	BE904724A (xx)
CA (1)	CA1278792C (xx)
CH (1)	CH672787A5 (xx)
DE (1)	DE3615180C2 (xx)
DK (1)	DK165745C (xx)
EG (1)	EG18206A (xx)
ES (6)	ES8801250A1 (xx)
FI (1)	FI85484C (xx)
FR (1)	FR2581385B1 (xx)
GB (1)	GB2174703B (xx)
GR (1)	GR861149B (xx)
HU (1)	HU195509B (xx)
IE (1)	IE59201B1 (xx)
IT (1)	IT1208607B (xx)
LU (1)	LU86421A1 (xx)
MY (1)	MY100777A (xx)
NL (1)	NL8601146A (xx)
PT (1)	PT82523B (xx)
SE (1)	SE465270B (xx)
ZA (1)	ZA862046B (xx)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5801186A (en) *	1987-11-20	1998-09-01	Hoechst Marion Roussel, Inc.	3- 4-(1-substituted-4-piperazinyl)butyl!-4-thiazolidinone and related compounds
US4880930A (en) *	1987-11-30	1989-11-14	New James S	Psychotropic acyclic amide derivatives
US4780466A (en) *	1988-03-17	1988-10-25	Hoechst-Roussel Pharmaceuticals, Inc.	Arylpiperazinylalkoxy derivatives of cyclic imides
IE903410A1 (en) *	1989-10-09	1991-04-10	Novo Nordisk As	Indole derivatives, their preparation and use
US5272148A (en) *	1992-09-09	1993-12-21	Hoechst-Roussel Pharmaceuticals Incorporated	Heteroarenylpiperazines
FR2738823B1 (fr) *	1995-09-15	1997-10-31	Synthelabo	Derives de 3-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)-3,4-dihydroquinolein-2(1h)-one,leur preparation et leur application en therapeutique
FR2738822B1 (fr) *	1995-09-15	1997-10-31	Synthelabo	Derives de 4-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique
FR2738824B1 (fr) *	1995-09-15	1997-10-31	Synthelabo	Derives de 3-(omega(4-(thieno(3,2-c)pyridin-4-yl)piperazin-1 -yl)alkyl)-3,4-dihydroquinazolin-2(1h)-one,leur preparation et leur application en therapeutique
SI0850235T1 (en) *	1995-09-15	2000-04-30	Sanofi-Synthelabo	Quinolein-2(1h)-one derivatives as serotonin antagonists
FR2761071B1 (fr) *	1997-03-20	1999-12-03	Synthelabo	Derives de quinolein-2(1h)-one et de dihydroquinolein-2(1h)- one, leur preparation et leur application en therapeutique
FR2797874B1 (fr) *	1999-08-27	2002-03-29	Adir	Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US20040077605A1 (en)	2001-06-20	2004-04-22	Salvati Mark E.	Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4367335A (en) *	1981-08-03	1983-01-04	Mead Johnson & Company	Thiazolidinylalkylene piperazine derivatives
US4452799A (en) *	1981-12-23	1984-06-05	Mead Johnson & Company	Benzisothiazole and benzisoxazole piperazine derivatives
US4361565A (en) *	1981-12-28	1982-11-30	Mead Johnson & Company	2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyridines

1986
- 1986-03-11 CA CA000503794A patent/CA1278792C/en not_active Expired - Fee Related
- 1986-03-19 ZA ZA862046A patent/ZA862046B/xx unknown
- 1986-04-29 AU AU56795/86A patent/AU593244B2/en not_active Expired
- 1986-04-29 EG EG250/86A patent/EG18206A/xx active
- 1986-04-29 GR GR861149A patent/GR861149B/el unknown
- 1986-04-30 FI FI861820A patent/FI85484C/fi not_active IP Right Cessation
- 1986-05-02 KR KR1019860003445A patent/KR940000829B1/ko not_active Expired - Fee Related
- 1986-05-02 GB GB08610810A patent/GB2174703B/en not_active Expired
- 1986-05-05 BE BE0/216623A patent/BE904724A/fr not_active IP Right Cessation
- 1986-05-05 FR FR8606471A patent/FR2581385B1/fr not_active Expired - Lifetime
- 1986-05-05 IE IE119386A patent/IE59201B1/en not_active IP Right Cessation
- 1986-05-05 NL NL8601146A patent/NL8601146A/nl active Search and Examination
- 1986-05-05 CN CN86103071A patent/CN1017901B/zh not_active Expired
- 1986-05-05 DE DE3615180A patent/DE3615180C2/de not_active Expired - Lifetime
- 1986-05-05 ES ES554659A patent/ES8801250A1/es not_active Expired
- 1986-05-05 DK DK207186A patent/DK165745C/da not_active IP Right Cessation
- 1986-05-05 LU LU86421A patent/LU86421A1/fr unknown
- 1986-05-05 SE SE8602061A patent/SE465270B/sv not_active IP Right Cessation
- 1986-05-05 CH CH1830/86A patent/CH672787A5/de not_active IP Right Cessation
- 1986-05-06 HU HU861860A patent/HU195509B/hu unknown
- 1986-05-06 JP JP61103726A patent/JPH0753728B2/ja not_active Expired - Lifetime
- 1986-05-06 IT IT8620313A patent/IT1208607B/it active
- 1986-05-06 PT PT82523A patent/PT82523B/pt unknown
- 1986-05-06 AT AT0121486A patent/AT398572B/de not_active IP Right Cessation
1987
- 1987-09-25 ES ES557757A patent/ES8802149A1/es not_active Expired
- 1987-10-01 MY MYPI87002712A patent/MY100777A/en unknown
1988
- 1988-01-28 ES ES557809A patent/ES8802614A1/es not_active Expired
- 1988-05-26 ES ES557839A patent/ES8900138A1/es not_active Expired
- 1988-11-16 ES ES557855A patent/ES8900253A1/es not_active Expired
1989
- 1989-02-27 ES ES557865A patent/ES9000005A1/es not_active Expired

Also Published As

Publication number	Publication date
FR2581385B1 (fr)	1991-10-04
DK165745C (da)	1993-06-14
PT82523A (en)	1986-06-01
PT82523B (pt)	1988-10-14
ES8802149A1 (es)	1988-04-01
KR860009008A (ko)	1986-12-19
CA1278792C (en)	1991-01-08
DE3615180C2 (de)	1996-03-07
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ES557855A0 (es)	1989-05-16
JPS61268681A (ja)	1986-11-28
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IT8620313A0 (it)	1986-05-06
ES554659A0 (es)	1987-12-16
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GB8610810D0 (en)	1986-06-11
CN1017901B (zh)	1992-08-19
EG18206A (en)	1992-09-30
ES8802614A1 (es)	1988-09-01
AU5679586A (en)	1986-11-13
FI85484C (fi)	1992-04-27
MY100777A (en)	1991-02-14
ES557839A0 (es)	1989-01-16
DK207186A (da)	1986-11-07
CH672787A5 (xx)	1989-12-29
FI861820A0 (fi)	1986-04-30
SE8602061D0 (sv)	1986-05-05
ES9000005A1 (es)	1989-11-01
GB2174703A (en)	1986-11-12
NL8601146A (nl)	1986-12-01
DK165745B (da)	1993-01-11
ES8900138A1 (es)	1989-01-16
KR940000829B1 (ko)	1994-02-02
ES8801250A1 (es)	1987-12-16
SE465270B (sv)	1991-08-19
BE904724A (fr)	1986-11-05
FI85484B (fi)	1992-01-15
CN86103071A (zh)	1987-03-18
ATA121486A (de)	1994-05-15
HUT43848A (en)	1987-12-28
IE59201B1 (en)	1994-01-26
JPH0753728B2 (ja)	1995-06-07
ES8900253A1 (es)	1989-05-16
AU593244B2 (en)	1990-02-08
FI861820A7 (fi)	1986-11-07
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IE861193L (en)	1986-11-06
SE8602061L (sv)	1986-11-07
DK207186D0 (da)	1986-05-05
LU86421A1 (fr)	1986-12-05
ZA862046B (en)	1986-11-26
GB2174703B (en)	1988-10-26
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IT1208607B (it)	1989-07-10

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1990-06-28	HU90	Patent valid on 900628