SU1048984A3 - Способ получени производных 2-/2-пиридил/-тетрагидротиофена или их солей - Google Patents

Способ получени производных 2-/2-пиридил/-тетрагидротиофена или их солей Download PDF

Info

Publication number: SU1048984A3
Authority: SU; USSR - Soviet Union
Prior art keywords: pyridyl; solution; tetrahydrothiophene; formula; temperature
Prior art date: 1980-01-24

Application number

SU802899103A

Other languages

English (en)

Spanish (es)

Russian (ru)

Inventor

Алу Жан-Клод

Бушодон Жан

Фарж Даниель

Жам Клод

Original Assignee

Рон-Пуленк Эндюстри (Фирма)

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.)

1980-01-24

Filing date

1980-03-27

Publication date

1983-10-15

1980-01-24 Priority claimed from FR8001499A external-priority patent/FR2474499A2/fr

1980-01-24 Priority claimed from FR8001500A external-priority patent/FR2474500A1/fr

1980-03-27 Application filed by Рон-Пуленк Эндюстри (Фирма) filed Critical Рон-Пуленк Эндюстри (Фирма)

1983-10-15 Application granted granted Critical

1983-10-15 Publication of SU1048984A3 publication Critical patent/SU1048984A3/ru

Links

238000000034 method Methods 0.000 title claims abstract description 9
150000003839 salts Chemical class 0.000 title claims abstract description 8
MCXIBJPBLIURRN-UHFFFAOYSA-N 2-(thiolan-2-yl)pyridine Chemical class C1CCSC1C1=CC=CC=N1 MCXIBJPBLIURRN-UHFFFAOYSA-N 0.000 title claims description 4
239000002904 solvent Substances 0.000 claims abstract description 12
-1 RADICAL BENZYL Chemical class 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
239000001257 hydrogen Substances 0.000 claims abstract 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
150000001412 amines Chemical class 0.000 claims abstract 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
150000003222 pyridines Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 4
239000002253 acid Substances 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
150000003254 radicals Chemical class 0.000 abstract 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
239000002184 metal Substances 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
239000003960 organic solvent Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 20
238000001914 filtration Methods 0.000 description 19
239000012153 distilled water Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000013078 crystal Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 12
238000001816 cooling Methods 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
235000013311 vegetables Nutrition 0.000 description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
239000000126 substance Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000000284 extract Substances 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
239000007788 liquid Substances 0.000 description 5
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 4
239000002245 particle Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
238000005303 weighing Methods 0.000 description 4
PAUTVGCJEKOAPC-UHFFFAOYSA-N 2-(3-chloropropylsulfanylmethyl)pyridine Chemical compound ClCCCSCC1=CC=CC=N1 PAUTVGCJEKOAPC-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000004071 soot Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
QHRRMDKSBSJPOU-UHFFFAOYSA-N CC1=CC=CC(SC(N)=N)=N1 Chemical compound CC1=CC=CC(SC(N)=N)=N1 QHRRMDKSBSJPOU-UHFFFAOYSA-N 0.000 description 2
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
235000011118 potassium hydroxide Nutrition 0.000 description 2
SJIIDWBFRZACDQ-UHFFFAOYSA-N pyridin-2-ylmethanethiol Chemical compound SCC1=CC=CC=N1 SJIIDWBFRZACDQ-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
IVSPJKRLTWBHHN-UHFFFAOYSA-N 1-sulfanyloxybutane Chemical compound CCCCOS IVSPJKRLTWBHHN-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
OMSBSIXAZZRIRW-UHFFFAOYSA-N 2-methylpyridine;hydrochloride Chemical compound Cl.CC1=CC=CC=N1 OMSBSIXAZZRIRW-UHFFFAOYSA-N 0.000 description 1
WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001262 anti-secretory effect Effects 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
DJFTXJLLHZRHKO-UHFFFAOYSA-N dipotassium oxygen(2-) hydrate Chemical compound O.[O--].[K+].[K+] DJFTXJLLHZRHKO-UHFFFAOYSA-N 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
OXPYXRLBNTVGFB-UHFFFAOYSA-N thiolane-2-carbothioamide Chemical compound NC(=S)C1CCCS1 OXPYXRLBNTVGFB-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

SU802899103A 1980-01-24 1980-03-27 Способ получени производных 2-/2-пиридил/-тетрагидротиофена или их солей SU1048984A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8001499A FR2474499A2 (fr)	1980-01-24	1980-01-24	Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent
FR8001500A FR2474500A1 (fr)	1980-01-24	1980-01-24	Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent

Publications (1)

Publication Number	Publication Date
SU1048984A3 true SU1048984A3 (ru)	1983-10-15

Family

ID=26221570

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU802899103A SU1048984A3 (ru)	1980-01-24	1980-03-27	Способ получени производных 2-/2-пиридил/-тетрагидротиофена или их солей

Country Status (4)

Country	Link
AT (1)	AT370101B (de)
CS (1)	CS228505B2 (de)
ES (1)	ES8105979A1 (de)
SU (1)	SU1048984A3 (de)

1980
- 1980-03-27 SU SU802899103A patent/SU1048984A3/ru active
- 1980-03-28 AT AT171480A patent/AT370101B/de not_active IP Right Cessation
- 1980-03-31 CS CS224480A patent/CS228505B2/cs unknown
- 1980-07-21 ES ES493554A patent/ES8105979A1/es not_active Expired

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. W.VJalter and 1-voss in The chemistry of amieles, ed. by I.Zabicky, I p., London, 1970, p. 422. *

Also Published As

Publication number	Publication date
ES493554A0 (es)	1981-07-01
CS228505B2 (en)	1984-05-14
AT370101B (de)	1983-03-10
ATA171480A (de)	1982-07-15
ES8105979A1 (es)	1981-07-01

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AU2007244358B2 (en)	2012-06-14	Amine derivative having NPY Y5 receptor antagonist activity
JPS6056143B2 (ja)	1985-12-09	アミジン誘導体ならびにその製造法
EP0927184B1 (de)	2003-10-22	3-substituierte pyrido 4',3':4,5] thieno 2,3-d]pyrimidin-derivate, ihre herstellung und verwendung
DK165693B (da)	1993-01-04	2-(n-substitueret guanidino)-4-heteroarylthiazol-forbindelser og farmaceutiske praeparater indeholdende disse
SU999972A3 (ru)	1983-02-23	Способ получени производных пиридо-(1,2-а) пиримидина или их фармацевтически приемлемых солей,или их оптически активных изомеров
SU1500158A3 (ru)	1989-08-07	Способ получени производного цинолина или его кислотно-аддитивных солей
NO172392B (no)	1993-04-05	Analogifremgangsmaate for fremstilling av 1h,3h-(1,2-c)-pyrrolo-7-tiazolkarboksamider
EP0262448A1 (de)	1988-04-06	Imidazolylguanidinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
NO762729L (de)	1977-02-08
CA1247101A (en)	1988-12-20	5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds, intermediates and methods for their preparation, and pharmaceutical compositions containing them
FI80025B (fi)	1989-12-29	Foerfarande foer framstaellning av blodtryckssaenkande n-piperazinylalkanoylanilider.
FI85484B (fi)	1992-01-15	Foerfarande foer framstaellning av antipsykotiska pyridinylpiperazinderivat som innehaoller en kondenserad ring.
NO172490B (no)	1993-04-19	Analogifremgangsmaate for fremstilling av terapeutisk aktive 1,4-disubstituerte piperazinderivater
SU1048984A3 (ru)	1983-10-15	Способ получени производных 2-/2-пиридил/-тетрагидротиофена или их солей
HU196377B (en)	1988-11-28	Process for production of 2-substituated-amin-5-acethilimidasoles
US3790586A (en)	1974-02-05	Imidazo-pyridine derivatives
DK169704B1 (da)	1995-01-16	Imidazoquinolinderivater, sådanne derivater til anvendelse som et anti-ulcusmiddel eller til behandling af hypersekretion samt farmaceutisk præparat indeholdende sådanne derivater
Kimura et al.	1992	Acridine derivatives. IV. Synthesis, molecular structure, and antitumor activity of the novel 9‐anilino‐2, 3‐methylenedioxyacridines
Timári et al.	1990	Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones
DE69003466T2 (de)	1994-01-20	Substituierte Thienopyrimidin-Derivate, deren Herstellung, pharmazeutische Zusammensetzungen und medizinische Verwendung.
Richardson Jr	1963	The Synthesis and Chemistry of Certain 2-Substituted 5, 6-Dihydroimidazo-,-oxazolo-, and-thiazolo [ij] quinolines
CA1175048A (en)	1984-09-25	2-cyclic amino-2-(1,2-benzisoxazol-3-yl)-acetic acid ester derivatives
SU908248A3 (ru)	1982-02-23	Способ получени дибензо- [а,D-ЦИКЛООКТЕН-6,12-ИМИНОВ ИЛИ ИХ ФАРМАЦЕВТИЧЕСКИ ПРИЕМЛЕМЫХ СОЛЕЙ
KR900004146B1 (ko)	1990-06-16	아릴 치환된 피리도[1,4]벤조디아제핀의 제조방법 및 그 제조중간체
CH643256A5 (de)	1984-05-30	4-oxo-4h-pyrido(1,2-a)pyrimidin-3-n(1h-tetrazol-5-yl)-carboxamide und verfahren zu ihrer herstellung.