CS271571B1 - Piperazine derivatives, their salts and method of their preparation - Google Patents

Piperazine derivatives, their salts and method of their preparation Download PDF

Info

Publication number: CS271571B1
Authority: CS; Czechoslovakia
Prior art keywords: formula; chloro; ethyl; dihydrodibenzo; compounds
Prior art date: 1987-12-10

Application number

CS879045A

Other languages

Czech (cs)

English (en)

Other versions

CS904587A1 (en

Inventor

Miroslav Dr Ing Drsc Protiva

Jiri Rndr Drsc Jilek

Martin Rndr Csc Valchar

Josef Pomykacek

Natasa Rndr Csc Dlohozkova

Original Assignee

Protiva Miroslav

Jilek Jiri

Valchar Martin

Josef Pomykacek

Dlohozkova Natasa

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.)

1987-12-10

Filing date

1987-12-10

Publication date

1990-10-12

1987-12-10 Application filed by Protiva Miroslav, Jilek Jiri, Valchar Martin, Josef Pomykacek, Dlohozkova Natasa filed Critical Protiva Miroslav

1987-12-10 Priority to CS879045A priority Critical patent/CS271571B1/cs

1988-11-19 Priority to JP63291117A priority patent/JPH01153685A/ja

1988-11-21 Priority to EP88310976A priority patent/EP0321100A3/fr

1990-02-12 Publication of CS904587A1 publication Critical patent/CS904587A1/cs

1990-10-12 Publication of CS271571B1 publication Critical patent/CS271571B1/cs

Links

238000000034 method Methods 0.000 title claims abstract description 18
150000003839 salts Chemical class 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 12
150000004885 piperazines Chemical class 0.000 title claims abstract description 10
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 12
SAHNLJYZUASUNV-UHFFFAOYSA-N 6-(2-bromoethoxy)-3-chloro-5,6-dihydrobenzo[b][1]benzothiepine Chemical compound BrCCOC1CC2=CC(Cl)=CC=C2SC2=CC=CC=C21 SAHNLJYZUASUNV-UHFFFAOYSA-N 0.000 claims abstract description 10
-1 2-(2-chloro-10,11-dihydrodibenzo(b,f)thiepin-10-yloxy)ethyl residue Chemical group 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 5
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims abstract description 3
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001414 amino alcohols Chemical class 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 51
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-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
235000005985 organic acids Nutrition 0.000 claims description 3
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
239000012346 acetyl chloride Substances 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
229940080818 propionamide Drugs 0.000 claims 1
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 10
238000006386 neutralization reaction Methods 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract description 6
230000001090 anti-dopaminergic effect Effects 0.000 abstract description 4
230000002908 adrenolytic effect Effects 0.000 abstract description 3
150000001805 chlorine compounds Chemical class 0.000 abstract description 3
LWEOFVINMVZGAS-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-ol Chemical compound OCCCN1CCNCC1 LWEOFVINMVZGAS-UHFFFAOYSA-N 0.000 abstract description 2
108090001111 Dopamine D2 Receptors Proteins 0.000 abstract description 2
102000004980 Dopamine D2 Receptors Human genes 0.000 abstract description 2
230000001078 anti-cholinergic effect Effects 0.000 abstract description 2
238000001727 in vivo Methods 0.000 abstract description 2
230000001624 sedative effect Effects 0.000 abstract description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 abstract 1
230000010933 acylation Effects 0.000 abstract 1
238000005917 acylation reaction Methods 0.000 abstract 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
239000000164 antipsychotic agent Substances 0.000 abstract 1
150000003840 hydrochlorides Chemical class 0.000 abstract 1
150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
239000000932 sedative agent Substances 0.000 abstract 1
150000003890 succinate salts Chemical class 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
239000002585 base Substances 0.000 description 17
239000000243 solution Substances 0.000 description 15
239000000126 substance Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
241000700159 Rattus Species 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
238000012360 testing method Methods 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 6
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 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
229960004046 apomorphine Drugs 0.000 description 4
230000002903 catalepsic effect Effects 0.000 description 4
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
210000001577 neostriatum Anatomy 0.000 description 4
239000000047 product Substances 0.000 description 4
RPXLXENSKHJVFW-UHFFFAOYSA-N 3-[4-[2-[(3-chloro-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)oxy]ethyl]piperazin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)CCN1CCOC1C2=CC=CC=C2SC2=CC=C(Cl)C=C2C1 RPXLXENSKHJVFW-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
239000001384 succinic acid Substances 0.000 description 3
IVTDFWJPURCKJY-UHFFFAOYSA-N 1-[2-[(3-chloro-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)oxy]ethyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCOC1C2=CC=CC=C2SC2=CC=C(Cl)C=C2C1 IVTDFWJPURCKJY-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
108050004812 Dopamine receptor Proteins 0.000 description 2
102000015554 Dopamine receptor Human genes 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
229960003638 dopamine Drugs 0.000 description 2
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 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
239000011976 maleic acid Substances 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000003389 potentiating effect Effects 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
239000002904 solvent Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000007306 turnover Effects 0.000 description 2
IKMKMRYGRAHTEF-UHFFFAOYSA-N 1-[2-[(3-chloro-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)oxy]ethyl]piperazine Chemical compound C1C2=CC(Cl)=CC=C2SC2=CC=CC=C2C1OCCN1CCNCC1 IKMKMRYGRAHTEF-UHFFFAOYSA-N 0.000 description 1
HTGCVLNFLVVCST-UHFFFAOYSA-N 1-piperazin-1-ylethanol Chemical class CC(O)N1CCNCC1 HTGCVLNFLVVCST-UHFFFAOYSA-N 0.000 description 1
CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 1
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
VVWMANLRLRFZIZ-UHFFFAOYSA-N 3-piperazin-1-ylpropanamide Chemical compound NC(=O)CCN1CCNCC1 VVWMANLRLRFZIZ-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
208000009132 Catalepsy Diseases 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
108090000511 Dopamine D1 Receptors Proteins 0.000 description 1
102000004076 Dopamine D1 Receptors Human genes 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
206010042008 Stereotypy Diseases 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
206010047853 Waxy flexibility Diseases 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003354 anti-apomorphinic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960003328 benzoyl peroxide Drugs 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical group BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
SXDQRQUWNQKZBL-UHFFFAOYSA-N butanedioic acid;hydrate Chemical compound O.OC(=O)CCC(O)=O SXDQRQUWNQKZBL-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
210000001653 corpus striatum Anatomy 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000706 effect on dopamine Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000005462 in vivo assay Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
231100000225 lethality Toxicity 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
230000000966 norepinephrine reuptake Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000005192 partition Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
230000000697 serotonin reuptake Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
108010092215 spiroperidol receptor Proteins 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (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)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

CS879045A 1987-12-10 1987-12-10 Piperazine derivatives, their salts and method of their preparation CS271571B1 (en)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CS879045A CS271571B1 (en)	1987-12-10	1987-12-10	Piperazine derivatives, their salts and method of their preparation
JP63291117A JPH01153685A (ja)	1987-12-10	1988-11-19	ピペラジン誘導体類及びそれらの酸付加塩類、及びそれらの調製方法
EP88310976A EP0321100A3 (fr)	1987-12-10	1988-11-21	Dérivés de pipérazine, leurs sels d'addition acide et procédé pour leur préparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS879045A CS271571B1 (en)	1987-12-10	1987-12-10	Piperazine derivatives, their salts and method of their preparation

Publications (2)

Publication Number	Publication Date
CS904587A1 CS904587A1 (en)	1990-02-12
CS271571B1 true CS271571B1 (en)	1990-10-12

Family

ID=5441754

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS879045A CS271571B1 (en)	1987-12-10	1987-12-10	Piperazine derivatives, their salts and method of their preparation

Country Status (3)

Country	Link
EP (1)	EP0321100A3 (fr)
JP (1)	JPH01153685A (fr)
CS (1)	CS271571B1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69426771T2 (de) *	1993-06-25	2001-06-13	Pola Chemical Industries, Inc.	Dopaminreinkorporationshemmer zur behandlung des parkinsonschen syndroms
AU4376997A (en) *	1996-10-04	1998-05-05	Novo Nordisk A/S	N-substituted azaheterocyclic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1247067A (en) *	1968-02-16	1971-09-22	Fujisawa Pharmaceutical Co	Tricyclic enol ether compounds and the preparation thereof

1987
- 1987-12-10 CS CS879045A patent/CS271571B1/cs unknown
1988
- 1988-11-19 JP JP63291117A patent/JPH01153685A/ja active Pending
- 1988-11-21 EP EP88310976A patent/EP0321100A3/fr not_active Withdrawn

Also Published As

Publication number	Publication date
CS904587A1 (en)	1990-02-12
EP0321100A3 (fr)	1990-08-01
EP0321100A2 (fr)	1989-06-21
JPH01153685A (ja)	1989-06-15

Publication	Publication Date	Title
US3420851A (en)	1969-01-07	Novel dibenzoxepines
NO174421B (no)	1994-01-24	Analogifremgangsmaate for fremstilling av den terapeutisk aktive forbindelsen 11-(4-(2-(2-hydroksyetoksy)-etyl)-1-piperazinyl)-dibenzo(b,f)(1,4)-tiazepin
EP0012385B1 (fr)	1983-02-16	Dibenz(b,f)(1,4)oxazépines, procédé pour leur préparation et compositions pharmaceutiques
US3192204A (en)	1965-06-29	Trifluoromethylthiaxanthene and -xanthene derivatives
IE58091B1 (en)	1993-06-30	1,4:3,6- dianhydrohexite derivatives, process for their preparation and their use as pharmaceuticals
US4025513A (en)	1977-05-24	Synthesis for the preparation of tetracyclic compounds
US4129565A (en)	1978-12-12	Isocarbostyril derivatives
EP0116368B1 (fr)	1987-10-28	Dérivés de benzothiazine
US3337554A (en)	1967-08-22	Piperazino and homopiperazino-10-11-dihydrobenzo[b, f]-thiepin
NO129043B (fr)	1974-02-18
US4213985A (en)	1980-07-22	Novel 5,11-dihydro-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-ones
DE69418321T2 (de)	1999-12-30	Tricyclische benzodiazepine, ihr verwendung und herstellung
NO831653L (no)	1983-05-10	Fremgangsmaate ved fremstilling av nye terapeutisk virksomme benzothiazolinforbindelser
EP0073645B1 (fr)	1986-11-12	Dérivés d'esters d'acides 2-cyclamino-2-(1,2-benzisoxazol-3-yl)-acétiques, procédé pour leur préparation et composition les contenant
US5736558A (en)	1998-04-07	4-(6-fluoro-1,2-benzisoxazolyl)-1 piperidinyl-propoxy-chromen-4-one-one-derivatives, their preparation and their use in the treatment of psychosis, schizophrenia and anxiety
EP0321100A2 (fr)	1989-06-21	Dérivés de pipérazine, leurs sels d'addition acide et procédé pour leur préparation
US3040031A (en)	1962-06-19	N-heterocyclic compounds
US3357982A (en)	1967-12-12	1-(5h-dibenzo [a, d] cyclohepten-5-yl)-4-alkylpiperazines
US3822267A (en)	1974-07-02	1 substituted 4 piperazino cycloalkylthiazoles
EP0034894A2 (fr)	1981-09-02	Dérivés 2-(1-pipérazinyl)-2,4,6-cycloheptatrién-1-one, procédés pour leur préparation, intermédiaires utilisés pour ces procédés et leur préparation et compositions pharmaceutiques les contenant
CS264541B1 (cs)	1989-08-14	Derivát 10-[2-(l-piperazinyl)ethoxy]-10,l l-dihydrodibenzo/b,f/thiepinu a jehc jantaran
SE441828B (sv)	1985-11-11	Nya dibenso/d,g//1,3,6/dioxazocinderivat
US6177566B1 (en)	2001-01-23	6-(4-arylalkylpiperazin-1-yl) benzodioxane and 6-(4-arylalkylpiperazin-1-yl) chromane derivatives: dopamine receptor subtype specific ligands
US3528970A (en)	1970-09-15	Aminomethyl derivatives of 9-cyclopropylmethylidene xanthenes and thioxanthenes
US3775415A (en)	1973-11-27	Lower-alkyl 6(or 7)-halo-5-(aminoalkylamino)-8-quinolinecarboxylates