SU733517A3 - Способ получени триазинонов - Google Patents

Способ получени триазинонов Download PDF

Info

Publication number: SU733517A3
Authority: SU; USSR - Soviet Union
Prior art keywords: het; general formula; triazin; methyl; mixture
Prior art date: 1977-03-19

Application number

SU782594701A

Other languages

German (de)

English (en)

Russian (ru)

Inventor

Генри Браун Томас

Джон Айф Роберт

Original Assignee

Смит Клайн Энд Френч Лабораториз Лтд (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.)

1977-03-19

Filing date

1978-03-17

Publication date

1980-05-05

1978-03-17 Application filed by Смит Клайн Энд Френч Лабораториз Лтд (Фирма) filed Critical Смит Клайн Энд Френч Лабораториз Лтд (Фирма)

1980-05-05 Application granted granted Critical

1980-05-05 Publication of SU733517A3 publication Critical patent/SU733517A3/ru

Links

238000000034 method Methods 0.000 title abstract description 4
150000003918 triazines Chemical class 0.000 title 1
-1 4-imidazolyl Chemical group 0.000 claims description 20
150000001412 amines Chemical class 0.000 claims description 5
238000002474 experimental method Methods 0.000 claims description 4
QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
UMCHIQCDVOOJLO-UHFFFAOYSA-N 2-[(3-bromopyridin-2-yl)methylsulfanyl]ethanamine Chemical compound NCCSCC1=NC=CC=C1Br UMCHIQCDVOOJLO-UHFFFAOYSA-N 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 6
238000002360 preparation method Methods 0.000 abstract description 3
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 abstract 2
150000003839 salts Chemical class 0.000 abstract 2
BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical class O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
150000007513 acids Chemical class 0.000 abstract 1
229960001340 histamine Drugs 0.000 abstract 1
229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 abstract 1
150000004677 hydrates Chemical class 0.000 abstract 1
239000000203 mixture Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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 4
238000001816 cooling Methods 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 2
QRICSZPYENRNSS-UHFFFAOYSA-N 3-(3-methoxyphenyl)-2-oxopropanoic acid Chemical compound COC1=CC=CC(CC(=O)C(O)=O)=C1 QRICSZPYENRNSS-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000003993 interaction Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000012265 solid product Substances 0.000 description 2
WCFWATIGPWBHRH-UHFFFAOYSA-N 3-methylsulfanyl-6-(pyridin-3-ylmethyl)-2h-1,2,4-triazin-5-one Chemical compound O=C1NC(SC)=NN=C1CC1=CC=CN=C1 WCFWATIGPWBHRH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910017435 S2 In Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5

Landscapes

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

SU782594701A 1977-03-19 1978-03-17 Способ получени триазинонов SU733517A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB11757/77A GB1601132A (en)	1977-03-19	1977-03-19	Pharmacologically active triazinones

Publications (1)

Publication Number	Publication Date
SU733517A3 true SU733517A3 (ru)	1980-05-05

Family

ID=9992150

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782594701A SU733517A3 (ru)	1977-03-19	1978-03-17	Способ получени триазинонов

Country Status (20)

Country	Link
AR (1)	AR223643A1 (fr)
BE (1)	BE864992A (fr)
BG (1)	BG33157A3 (fr)
CS (1)	CS208746B2 (fr)
DD (1)	DD134522A5 (fr)
DK (1)	DK121978A (fr)
EG (1)	EG13240A (fr)
ES (1)	ES467953A1 (fr)
FI (1)	FI780629A7 (fr)
GB (1)	GB1601132A (fr)
GR (1)	GR66122B (fr)
HU (1)	HU175669B (fr)
IT (1)	IT1095458B (fr)
NO (1)	NO148556C (fr)
PL (1)	PL110686B1 (fr)
PT (1)	PT67687B (fr)
SE (1)	SE7803113L (fr)
SU (1)	SU733517A3 (fr)
YU (1)	YU65278A (fr)
ZA (1)	ZA78988B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4309435A (en)	1978-10-16	1982-01-05	Imperial Chemical Industries Ltd.	Antisecretory guanidine derivatives and pharmaceutical compositions containing them
US4394508A (en) *	1980-06-07	1983-07-19	Bristol-Myers Company	Chemical compounds
AU2192683A (en) *	1982-12-30	1984-07-05	Biomeasure Incorporated	Pyrazolo(1,5-alpha)-1,3,5-triazines
GB0113343D0 (en) *	2001-06-01	2001-07-25	Bayer Ag	Novel Heterocycles 2

1977
- 1977-03-19 GB GB11757/77A patent/GB1601132A/en not_active Expired
1978
- 1978-02-20 ZA ZA00780988A patent/ZA78988B/xx unknown
- 1978-02-22 PT PT67687A patent/PT67687B/pt unknown
- 1978-02-24 FI FI780629A patent/FI780629A7/fi not_active Application Discontinuation
- 1978-02-28 IT IT20754/78A patent/IT1095458B/it active
- 1978-03-06 GR GR55622A patent/GR66122B/el unknown
- 1978-03-13 CS CS781576A patent/CS208746B2/cs unknown
- 1978-03-16 BE BE186018A patent/BE864992A/fr not_active IP Right Cessation
- 1978-03-17 HU HUSI001621 patent/HU175669B/hu unknown
- 1978-03-17 BG BG039077A patent/BG33157A3/xx unknown
- 1978-03-17 DD DD78204258A patent/DD134522A5/xx unknown
- 1978-03-17 PL PL1978205382A patent/PL110686B1/pl unknown
- 1978-03-17 NO NO780970A patent/NO148556C/no unknown
- 1978-03-17 AR AR271459A patent/AR223643A1/es active
- 1978-03-17 YU YU00652/78A patent/YU65278A/xx unknown
- 1978-03-17 SE SE7803113A patent/SE7803113L/xx unknown
- 1978-03-17 SU SU782594701A patent/SU733517A3/ru active
- 1978-03-17 ES ES467953A patent/ES467953A1/es not_active Expired
- 1978-03-17 DK DK121978A patent/DK121978A/da not_active Application Discontinuation
- 1978-03-18 EG EG180/78A patent/EG13240A/xx active

Also Published As

Publication number	Publication date
PT67687A (en)	1978-03-01
ES467953A1 (es)	1978-11-01
NO780970L (no)	1978-09-20
PL110686B1 (en)	1980-07-31
BG33157A3 (bg)	1982-12-15
GR66122B (fr)	1981-01-16
PT67687B (en)	1979-07-23
EG13240A (en)	1980-12-31
PL205382A1 (pl)	1979-03-26
IT7820754A0 (it)	1978-02-28
DD134522A5 (de)	1979-03-07
FI780629A7 (fi)	1978-09-20
YU65278A (en)	1982-08-31
GB1601132A (en)	1981-10-28
ZA78988B (en)	1979-06-27
AR223643A1 (es)	1981-09-15
IT1095458B (it)	1985-08-10
BE864992A (fr)	1978-09-18
HU175669B (fr)	1980-09-28
NO148556B (no)	1983-07-25
SE7803113L (sv)	1978-09-20
NO148556C (no)	1983-11-02
CS208746B2 (en)	1981-09-15
DK121978A (da)	1978-09-20

Publication	Publication Date	Title
AT390257B (de)	1990-04-10	Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate
DE69303191T2 (de)	1996-11-14	Naphthalinderivate, ihre Herstellungsverfahren und synthetische Zwischenprodukte dafür
DE602004011966T2 (de)	2009-02-12	Heterocyclylverbindungen
US3993656A (en)	1976-11-23	1,8-Naphthyridine compounds
DD251971A5 (de)	1987-12-02	Verfahren zur herstellung einer pharmazeutisch aktiven oxindol-verbindung
SU733517A3 (ru)	1980-05-05	Способ получени триазинонов
HU180081B (en)	1983-01-28	Process for producing hystamine antagonic 2-amino-pirimidone derivatives
CS183491A3 (en)	1992-01-15	Process for preparing dialkylpyridine-2,3-dicarboxylates and derivatives thereof
US4412077A (en)	1983-10-25	Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinone
US4524149A (en)	1985-06-18	5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use
EP1928833B1 (fr)	2009-02-18	Nouveaux dérivés de quinoline susceptibles de se lier au récepteur cb2
US4504482A (en)	1985-03-12	[5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof
SU460624A3 (ru)	1975-02-15	Способ получени пиридилпиперазинов или их солей
US3201406A (en)	1965-08-17	Pyridylcoumarins
JPH0331265A (ja)	1991-02-12	テトラヒドロピリミジン誘導体の製造方法
DE1965981C3 (de)	1978-08-31	9-Phenyl-lO-oxopiperazino [l,2-a]-indole und Verfahren zu ihrer Herstellung
Moffett	1970	Azacoumarins
SU455533A3 (ru)	1974-12-30	Способ получени производных 4-хлор-5-сульфамоилантраниловой кислоты
DE2105191A1 (de)	1971-08-26	2 Tetrazolylchromondenvate, Ver fahren zu ihrer Herstellung und Arznei praparate
CA1166253A (fr)	1984-04-24	4-amino-6-(pyridinyl)-3(2h)-pyridazinones, preparation et utilisation comme agents cardiotoniques
SU564809A3 (ru)	1977-07-05	Способ получени 6-аза-1,2дигидро-3н-1,4-бензодиазепинов или их солей
DE1813241C3 (fr)	1978-02-02
EP0011282A1 (fr)	1980-05-28	Dérivés de l'acide thiénylbenzoique, procédé pour leur préparation, préparations pharmaceutiques à base de ces composés
US4255581A (en)	1981-03-10	Process for the preparation of alkyl and aryl esters of 3'-substituted and 2', 3'-disubstituted 2-anilino-3-pyridinecarboxylic acids
DE1695188C3 (de)	1980-12-11	Verfahren zur Herstellung von l-Alkyl^-chlor^-dihydro-S-phenyl-IH-1,4-benzodiazepinen