OA11041A - 2-Methoxyphenylpiperazine derivatives - Google Patents

2-Methoxyphenylpiperazine derivatives Download PDF

Info

Publication number: OA11041A
Authority: OA; OAPI
Prior art keywords: imidazo; formula; indolizinyl; compound; phenoxy
Prior art date: 1996-10-30

Application number

OA9900092A

Other languages

English (en)

Inventor

Istvan Laszlovszky

Gyoergy Domany

Tibor Acs

Gyoergy Ferenczy

Szantay Csaba Jr

Eszter Thuroczyne Kalkman

Erzsebet Lapis

Ferenc Trischler

Bela Hegedus

Ferenc Auth

Monika Csejtei

Egon Karpati

Bela Kiss

Judit Laszy

Margit Pellioniszne Paroczai

Adam Sarkadi

Sandor Szabo

Original Assignee

Richter Gedeon Vegyeszet

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.)

1996-10-30

Filing date

1999-04-30

Publication date

2003-03-07

1999-04-30 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

2003-03-07 Publication of OA11041A publication Critical patent/OA11041A/en

Links

VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical class COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 76
-1 2-indolizinyl Chemical group 0.000 claims abstract description 40
238000000034 method Methods 0.000 claims abstract description 29
239000000203 mixture Substances 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 7
201000000980 schizophrenia Diseases 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
230000008569 process Effects 0.000 claims abstract description 5
208000019901 Anxiety disease Diseases 0.000 claims abstract description 4
208000019022 Mood disease Diseases 0.000 claims abstract description 4
208000027626 Neurocognitive disease Diseases 0.000 claims abstract description 4
150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
208000022821 personality disease Diseases 0.000 claims abstract description 3
230000036506 anxiety Effects 0.000 claims abstract 3
125000000335 thiazolyl group Chemical group 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
208000035475 disorder Diseases 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
230000000561 anti-psychotic effect Effects 0.000 abstract description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 34
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 22
230000000694 effects Effects 0.000 description 18
229960004170 clozapine Drugs 0.000 description 11
QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 11
KNWASYXLJCYACD-UHFFFAOYSA-N 2-[4-(2-chloroethoxy)phenyl]indolizine Chemical compound C1=CC(OCCCl)=CC=C1C1=CN2C=CC=CC2=C1 KNWASYXLJCYACD-UHFFFAOYSA-N 0.000 description 10
239000000155 melt Substances 0.000 description 10
102000005962 receptors Human genes 0.000 description 9
108020003175 receptors Proteins 0.000 description 9
239000007858 starting material Substances 0.000 description 9
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 8
229960004046 apomorphine Drugs 0.000 description 8
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 7
101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000000126 substance Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
208000027776 Extrapyramidal disease Diseases 0.000 description 5
239000003693 atypical antipsychotic agent Substances 0.000 description 5
229940127236 atypical antipsychotics Drugs 0.000 description 5
230000009194 climbing Effects 0.000 description 5
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000164 antipsychotic agent Substances 0.000 description 4
229940005529 antipsychotics Drugs 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
230000010534 mechanism of action Effects 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000009471 action Effects 0.000 description 3
230000027455 binding 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
229960003878 haloperidol Drugs 0.000 description 3
239000003446 ligand Substances 0.000 description 3
230000002197 limbic effect Effects 0.000 description 3
230000009871 nonspecific binding Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
101150049660 DRD2 gene Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010042008 Stereotypy Diseases 0.000 description 2
230000002411 adverse Effects 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
230000003920 cognitive function Effects 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
229960003750 ethyl chloride Drugs 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000011160 research Methods 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229940083599 sodium iodide Drugs 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
238000012360 testing method Methods 0.000 description 2
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
BYVYSAZPJWCRCG-UHFFFAOYSA-N 2-[4-(2-chloroethoxy)phenyl]imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OCCCl)=CC=C1C1=CN(C=CC=N2)C2=N1 BYVYSAZPJWCRCG-UHFFFAOYSA-N 0.000 description 1
GSEZHQBHGMMKBC-UHFFFAOYSA-N 2-[4-(3-chloropropoxy)phenyl]imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OCCCCl)=CC=C1C1=CN(C=CC=N2)C2=N1 GSEZHQBHGMMKBC-UHFFFAOYSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
BVLWMAVGQBIIRG-UHFFFAOYSA-N 2-[4-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy]phenyl]indolizine Chemical compound COC1=CC=CC=C1N1CCN(CCOC=2C=CC(=CC=2)C2=CN3C=CC=CC3=C2)CC1 BVLWMAVGQBIIRG-UHFFFAOYSA-N 0.000 description 1
HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
RWJISOGZLLCXBJ-UHFFFAOYSA-N 6-[4-(3-chloropropoxy)phenyl]imidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(OCCCCl)=CC=C1C1=CN(C=CS2)C2=N1 RWJISOGZLLCXBJ-UHFFFAOYSA-N 0.000 description 1
206010001497 Agitation Diseases 0.000 description 1
206010003805 Autism Diseases 0.000 description 1
208000020706 Autistic disease Diseases 0.000 description 1
208000020925 Bipolar disease Diseases 0.000 description 1
206010012218 Delirium Diseases 0.000 description 1
206010012239 Delusion Diseases 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
206010012335 Dependence Diseases 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000004547 Hallucinations Diseases 0.000 description 1
206010021118 Hypotonia Diseases 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
206010026749 Mania Diseases 0.000 description 1
208000036626 Mental retardation Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000007379 Muscle Hypotonia Diseases 0.000 description 1
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
206010034912 Phobia Diseases 0.000 description 1
208000001431 Psychomotor Agitation Diseases 0.000 description 1
206010037211 Psychomotor hyperactivity Diseases 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
230000001154 acute effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
230000008061 calcium-channel-blocking effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
231100000868 delusion Toxicity 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
208000024732 dysthymic disease Diseases 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
208000037870 generalized anxiety Diseases 0.000 description 1
CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
230000000324 neuroprotective effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
230000002746 orthostatic effect Effects 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
150000002990 phenothiazines Chemical class 0.000 description 1
208000019899 phobic disease Diseases 0.000 description 1
239000006187 pill Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229960001289 prazosin Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
230000000087 stabilizing effect Effects 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
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
229960004940 sulpiride Drugs 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000003826 tablet Substances 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
238000002560 therapeutic procedure Methods 0.000 description 1
208000016686 tic disease Diseases 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

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

OA9900092A 1996-10-30 1999-04-30 2-Methoxyphenylpiperazine derivatives OA11041A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU9603001A HUP9603001A3 (en)	1996-10-30	1996-10-30	Heterocycle compounds comprising nitrogen, process for producing them and pharmaceutical compositions containing the same

Publications (1)

Publication Number	Publication Date
OA11041A true OA11041A (en)	2003-03-07

Family

ID=89994394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900092A OA11041A (en)	1996-10-30	1999-04-30	2-Methoxyphenylpiperazine derivatives

Country Status (25)

Country	Link
US (1)	US6103724A (is)
EP (1)	EP0935599A1 (is)
JP (1)	JP2001503048A (is)
KR (1)	KR20000052872A (is)
CN (1)	CN1235606A (is)
AP (1)	AP9901532A0 (is)
AR (1)	AR010260A1 (is)
AU (1)	AU4962097A (is)
BG (1)	BG103370A (is)
BR (1)	BR9712588A (is)
CA (1)	CA2269814A1 (is)
CZ (1)	CZ132099A3 (is)
EA (1)	EA199900433A1 (is)
EE (1)	EE9900182A (is)
HU (1)	HUP9603001A3 (is)
IL (1)	IL129418A0 (is)
IS (1)	IS5026A (is)
NO (1)	NO992059L (is)
OA (1)	OA11041A (is)
PL (1)	PL333076A1 (is)
SK (1)	SK49499A3 (is)
TR (1)	TR199900946T2 (is)
TW (1)	TW406083B (is)
WO (1)	WO1998018797A1 (is)
ZA (1)	ZA979617B (is)

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US7253165B2 (en) *	1999-09-14	2007-08-07	Aventis Pharmaceuticals Inc.	Benzisoxazolyl-, pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists
US7125903B1 (en)	1999-09-14	2006-10-24	Aventis Pharmaceuticals Inc.	Thienoisoxazolyl-and thienylpyrrazolyl-phenoxy substituted propyl derivatives useful as D4 antagonists
PT1216249E (pt) *	1999-09-14	2004-04-30	Aventis Pharma Inc	Derivados de etilicos e propilicos insubstituidos de tienoisoxazol-fenoxi uteis como antagonistas d4
DK1216250T3 (da) *	1999-09-14	2004-02-23	Aventis Pharma Inc	Thienoisoxazolyl- og thienylpyrazolyl-phenoxy- substituerede propylderivater som D4-antagonister
US7091199B1 (en)	1999-09-14	2006-08-15	Aventis Pharmaceuticals Inc.	Thienoisoxazole phenoxy unsubstituted ethyl and propyl derivatives useful as d4 antagonists
ATE361297T1 (de)	2000-03-31	2007-05-15	Ortho Mcneil Pharm Inc	Phenyl-substituierte imidazopyridine
TW200811175A (en) *	2006-06-21	2008-03-01	Nihon Mediphysics Co Ltd	Novel compound with affinity with amyloid
AU2008314870A1 (en) *	2007-10-24	2009-04-30	Nihon Medi-Physics Co., Ltd.	Novel compound having affinity for amyloid
AU2008314871A1 (en) *	2007-10-26	2009-04-30	Nihon Medi-Physics Co., Ltd.	Novel compound having affinity for amyloid
US7964605B2 (en) *	2008-05-29	2011-06-21	Sk Holdings Co., Ltd.	Phenyl piperazine compounds, pharmaceutical composition comprising the same, and use thereof
US7985752B2 (en)	2008-05-29	2011-07-26	Sk Holdings Co., Ltd.	Phenyl piperazine compounds, pharmaceutical composition including the same and use thereof
CN106187873B (zh) *	2016-07-25	2019-11-05	宜春学院	一种芳胺基烷基氧类化合物及其制备方法

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US4880824A (en) *	1987-09-21	1989-11-14	Ortho Pharmaceutical Corporation	Phenyl and benzoyl substituted imidazo-fused heterocyclic calcium channel blockers
EP0591528B1 (en) *	1991-04-22	1998-12-23	Otsuka Pharmaceutical Factory, Inc.	PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE AND ANTI-INFLAMMATORY CONTAINING THE SAME
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US6013654A (en) *	1997-08-14	2000-01-11	Pharmacia & Upjohn Company	Imidazo[1,2-A]pyridines for the treatment of CNS and cardiac diseases

1996
- 1996-10-30 HU HU9603001A patent/HUP9603001A3/hu unknown
1997
- 1997-10-22 IL IL12941897A patent/IL129418A0/xx unknown
- 1997-10-22 BR BR9712588-1A patent/BR9712588A/pt not_active Application Discontinuation
- 1997-10-22 EP EP97912393A patent/EP0935599A1/en not_active Withdrawn
- 1997-10-22 AU AU49620/97A patent/AU4962097A/en not_active Abandoned
- 1997-10-22 WO PCT/HU1997/000069 patent/WO1998018797A1/en not_active Ceased
- 1997-10-22 KR KR1019990703721A patent/KR20000052872A/ko not_active Withdrawn
- 1997-10-22 EE EEP199900182A patent/EE9900182A/xx unknown
- 1997-10-22 AP APAP/P/1999/001532A patent/AP9901532A0/en unknown
- 1997-10-22 EA EA199900433A patent/EA199900433A1/ru unknown
- 1997-10-22 SK SK494-99A patent/SK49499A3/sk unknown
- 1997-10-22 PL PL97333076A patent/PL333076A1/xx unknown
- 1997-10-22 CA CA002269814A patent/CA2269814A1/en not_active Abandoned
- 1997-10-22 CN CN97199313A patent/CN1235606A/zh active Pending
- 1997-10-22 JP JP10520214A patent/JP2001503048A/ja active Pending
- 1997-10-22 CZ CZ991320A patent/CZ132099A3/cs unknown
- 1997-10-22 US US09/284,313 patent/US6103724A/en not_active Expired - Fee Related
- 1997-10-22 TR TR1999/00946T patent/TR199900946T2/xx unknown
- 1997-10-27 ZA ZA9709617A patent/ZA979617B/xx unknown
- 1997-10-31 AR ARP970105061A patent/AR010260A1/es unknown
- 1997-11-17 TW TW086117150A patent/TW406083B/zh active
1999
- 1999-04-15 IS IS5026A patent/IS5026A/is unknown
- 1999-04-29 NO NO992059A patent/NO992059L/no not_active Application Discontinuation
- 1999-04-29 BG BG103370A patent/BG103370A/bg unknown
- 1999-04-30 OA OA9900092A patent/OA11041A/en unknown

Also Published As

Publication number	Publication date
HUP9603001A2 (hu)	1998-07-28
NO992059D0 (no)	1999-04-29
WO1998018797A1 (en)	1998-05-07
EP0935599A1 (en)	1999-08-18
BR9712588A (pt)	1999-10-26
CN1235606A (zh)	1999-11-17
NO992059L (no)	1999-04-29
ZA979617B (en)	1998-05-21
HU9603001D0 (en)	1996-12-30
AU4962097A (en)	1998-05-22
TR199900946T2 (xx)	1999-07-21
US6103724A (en)	2000-08-15
IL129418A0 (en)	2000-02-17
HUP9603001A3 (en)	1999-07-28
AR010260A1 (es)	2000-06-07
AP9901532A0 (en)	1999-06-30
BG103370A (bg)	2000-05-31
KR20000052872A (ko)	2000-08-25
IS5026A (is)	1999-04-15
EA199900433A1 (ru)	1999-10-28
SK49499A3 (en)	2000-03-13
JP2001503048A (ja)	2001-03-06
EE9900182A (et)	1999-12-15
PL333076A1 (en)	1999-11-08
TW406083B (en)	2000-09-21
CZ132099A3 (cs)	1999-08-11
CA2269814A1 (en)	1998-05-07

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RU2715421C2 (ru)	2020-02-28	Тетрагидропиранил амино-пирролопиримидинон и способы его применения
US6284757B1 (en)	2001-09-04	Pyrrolo[1,2-a]pyrazine derivatives as 5HT1A ligands
EP1417206B1 (en)	2010-05-05	Novel 2h-pyridazine-3-one derivatives, pharmaceutical compositions containing the same and a process for the preparation of the active ingredient
RU2485116C2 (ru)	2013-06-20	Производные 4-пиримидинсульфамида
AU2016299092B2 (en)	2020-08-20	1, 3, 5-triazine derivative and method of using same
OA11041A (en)	2003-03-07	2-Methoxyphenylpiperazine derivatives
KR19980074060A (ko)	1998-11-05	신규한 치환된 3,4-디알콕시페닐 유도체
CS241549B2 (en)	1986-03-13	Method of 1,4-dihydropyridines production
EP3700895B1 (en)	2021-09-22	Polycyclic amides as muscarinic m1 receptor positive allosteric modulators
JPH05117268A (ja)	1993-05-14	ピリジン化合物
JPS62120374A (ja)	1987-06-01	１，３−チアジンまたは１，３−オキサジン誘導体
US4493837A (en)	1985-01-15	Theobromine derivatives
US20110172280A1 (en)	2011-07-14	Substituted Benzimidazoles
US11401261B2 (en)	2022-08-02	2-heteroaryl aminoquinazolinone derivative
US12404268B2 (en)	2025-09-02	2-heteroaryl aminoquinazolinone derivative
JPH0495071A (ja)	1992-03-27	カルバミン酸誘導体
EP1098888A1 (fr)	2001-05-16	Derives de piperazinones et leurs applications
MXPA99004015A (en)	2000-09-04	2-methoxyphenylpiperazine derivatives
HK40082180A (en)	2023-06-02	2-heteroarylaminoquinazolinone derivative
JPH0443913B2 (is)	1992-07-20
HK1067626B (en)	2010-10-15	Novel 2h-pyridazine-3-one derivatives, pharmaceutical compositions containing the same and a process for the preparation of the active ingredient
JPH0242078A (ja)	1990-02-13	縮合複素環化合物
JPS63107975A (ja)	1988-05-12	ジヒドロピリジン誘導体および医薬組成物
JPH10120632A (ja)	1998-05-12	Ｎ−シクロアルキル−〔ω−（３，４−ジヒドロ−２−ナフタレニル）アルキル〕アミン誘導体及びそれを含有する医薬組成物