CS241471B2 - Způsob výroby pyrimido-2-benzazepinů - Google Patents

Způsob výroby pyrimido-2-benzazepinů Download PDF

Info

Publication number: CS241471B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; chloro; group; pyrimido; hydrogen
Prior art date: 1979-02-07

Application number

CS80799A

Other languages

Czech (cs)

English (en)

Other versions

CS79980A2 (en

Inventor

Rodney I Fryer

Norman W Gilman

Eugens J Trybulski

Armin Walser

Original Assignee

Hoffmann La Roche

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.)

1979-02-07

Filing date

1980-02-06

Publication date

1986-03-13

1980-02-06 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1985-07-16 Publication of CS79980A2 publication Critical patent/CS79980A2/cs

1986-03-13 Publication of CS241471B2 publication Critical patent/CS241471B2/cs

Links

238000000034 method Methods 0.000 title claims description 14
SYYWEHJLUMPGIZ-UHFFFAOYSA-N C1=CC=NC=C2C3=CNC=NC3=CC=C21 Chemical class C1=CC=NC=C2C3=CNC=NC3=CC=C21 SYYWEHJLUMPGIZ-UHFFFAOYSA-N 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
-1 α-hydroxyethyl group Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
XUUSYXJGMRQBKQ-UHFFFAOYSA-N 2h-2-benzazepine Chemical compound N1C=CC=C2C=CC=CC2=C1 XUUSYXJGMRQBKQ-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
MCUPNPQIJUEVRX-UHFFFAOYSA-N 9-chloro-7-(2-chlorophenyl)-2-methyl-5h-pyrimido[5,4-d][2]benzazepine Chemical compound C12=CC(Cl)=CC=C2C2=NC(C)=NC=C2CN=C1C1=CC=CC=C1Cl MCUPNPQIJUEVRX-UHFFFAOYSA-N 0.000 claims description 3
FXBGWQBBFOHQAR-UHFFFAOYSA-N 9-chloro-7-(2-fluorophenyl)-n,n-dimethyl-5h-pyrimido[5,4-d][2]benzazepin-2-amine Chemical compound C12=CC(Cl)=CC=C2C2=NC(N(C)C)=NC=C2CN=C1C1=CC=CC=C1F FXBGWQBBFOHQAR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
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239000000203 mixture Substances 0.000 description 44
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238000001953 recrystallisation Methods 0.000 description 18
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238000003756 stirring Methods 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
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239000011541 reaction mixture Substances 0.000 description 9
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239000000047 product Substances 0.000 description 8
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229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
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125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
FBRAIVNJLBZIIY-UHFFFAOYSA-N 9-chloro-7-(2-fluorophenyl)-5h-pyrimido[5,4-d][2]benzazepin-2-amine Chemical compound C12=CC(Cl)=CC=C2C2=NC(N)=NC=C2CN=C1C1=CC=CC=C1F FBRAIVNJLBZIIY-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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 5
XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 5
239000008101 lactose Substances 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
AQNQKCGTJAKHLW-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-4-(dimethylaminomethylidene)-3h-2-benzazepin-5-one Chemical compound C12=CC(Cl)=CC=C2C(=O)C(=CN(C)C)CN=C1C1=CC=CC=C1Cl AQNQKCGTJAKHLW-UHFFFAOYSA-N 0.000 description 4
BZXFISJCUDAPKZ-UHFFFAOYSA-N 8-chloro-4-(dimethylaminomethylidene)-1-(2-fluorophenyl)-2-oxido-3h-2-benzazepin-2-ium-5-one Chemical compound C12=CC(Cl)=CC=C2C(=O)C(=CN(C)C)C[N+]([O-])=C1C1=CC=CC=C1F BZXFISJCUDAPKZ-UHFFFAOYSA-N 0.000 description 4
XTRICTUJBXEEFH-UHFFFAOYSA-N 8-chloro-4-(dimethylaminomethylidene)-1-(2-fluorophenyl)-3h-2-benzazepin-5-one Chemical compound C12=CC(Cl)=CC=C2C(=O)C(=CN(C)C)CN=C1C1=CC=CC=C1F XTRICTUJBXEEFH-UHFFFAOYSA-N 0.000 description 4
GBTZWDORYJOWFT-UHFFFAOYSA-N 8-chloro-4-(dimethylaminomethylidene)-1-phenyl-3h-2-benzazepin-5-one Chemical compound C12=CC(Cl)=CC=C2C(=O)C(=CN(C)C)CN=C1C1=CC=CC=C1 GBTZWDORYJOWFT-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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238000009835 boiling Methods 0.000 description 4
239000002775 capsule Substances 0.000 description 4
SUCKKDRJRWHVKQ-UHFFFAOYSA-N 7-phenyl-5,6-dihydropyrimido[5,4-d][1]benzazepin-2-amine Chemical compound C12=CC=CC=C2C2=NC(N)=NC=C2CCN1C1=CC=CC=C1 SUCKKDRJRWHVKQ-UHFFFAOYSA-N 0.000 description 3
MXBMBCKVMVLOBI-UHFFFAOYSA-N 8-chloro-1-(2-fluorophenyl)-3,4-dihydro-2-benzazepin-5-one Chemical compound FC1=CC=CC=C1C1=NCCC(=O)C2=CC=C(Cl)C=C12 MXBMBCKVMVLOBI-UHFFFAOYSA-N 0.000 description 3
CLYXKIKVKJZIOF-UHFFFAOYSA-N 9-chloro-7-(2-chlorophenyl)-5h-pyrimido[5,4-d][2]benzazepine Chemical compound C=1C(Cl)=CC=C(C2=NC=NC=C2CN=2)C=1C=2C1=CC=CC=C1Cl CLYXKIKVKJZIOF-UHFFFAOYSA-N 0.000 description 3
UOMNACAACGEPRY-UHFFFAOYSA-N 9-chloro-7-(2-fluorophenyl)-5h-pyrimido[5,4-d][2]benzazepine Chemical compound FC1=CC=CC=C1C1=NCC2=CN=CN=C2C2=CC=C(Cl)C=C12 UOMNACAACGEPRY-UHFFFAOYSA-N 0.000 description 3
NBDMULRONZEXNZ-UHFFFAOYSA-N 9-chloro-7-(2-fluorophenyl)-6-oxido-5h-pyrimido[5,4-d][2]benzazepin-6-ium-2-amine Chemical compound C12=CC(Cl)=CC=C2C2=NC(N)=NC=C2C[N+]([O-])=C1C1=CC=CC=C1F NBDMULRONZEXNZ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
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239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
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150000001409 amidines Chemical class 0.000 description 2
239000002249 anxiolytic agent Substances 0.000 description 2
230000000949 anxiolytic effect Effects 0.000 description 2
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229910052786 argon Inorganic materials 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
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150000008282 halocarbons Chemical class 0.000 description 2
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229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
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239000008194 pharmaceutical composition Substances 0.000 description 2
229940125723 sedative agent Drugs 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
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238000004809 thin layer chromatography Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
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CUJJWOUYYROEOP-UHFFFAOYSA-N 2-benzazepin-2-amine Chemical compound NN1C=CC=C2C=CC=CC2=C1 CUJJWOUYYROEOP-UHFFFAOYSA-N 0.000 description 1
ADZBILKIFSTUEQ-UHFFFAOYSA-N 2-methyl-7-phenyl-5h-pyrimido[5,4-d][2]benzazepine;dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2C2=NC(C)=NC=C2CN=C1C1=CC=CC=C1 ADZBILKIFSTUEQ-UHFFFAOYSA-N 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OGHNOZVPESJECR-UHFFFAOYSA-N C=C1C2=CC=CC=C2C(=O)C=CN1 Chemical compound C=C1C2=CC=CC=C2C(=O)C=CN1 OGHNOZVPESJECR-UHFFFAOYSA-N 0.000 description 1
KZFCKDMGZONFSY-UHFFFAOYSA-N CN(C)C1C(=C)N=C(C2=C(C1=O)C=CC(=C2)Cl)C3=CC=CC=C3Cl Chemical compound CN(C)C1C(=C)N=C(C2=C(C1=O)C=CC(=C2)Cl)C3=CC=CC=C3Cl KZFCKDMGZONFSY-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
240000006890 Erythroxylum coca Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 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
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000004368 Modified starch Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000008957 cocaer Nutrition 0.000 description 1
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000003226 decolorizating effect Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000011282 treatment Methods 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS80799A 1979-02-07 1980-02-06 Způsob výroby pyrimido-2-benzazepinů CS241471B2 (cs)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US1011879A	1979-02-07	1979-02-07
US1670979A	1979-03-01	1979-03-01
CH51180		1980-01-22

Publications (2)

Publication Number	Publication Date
CS79980A2 CS79980A2 (en)	1985-07-16
CS241471B2 true CS241471B2 (cs)	1986-03-13

Family

ID=27172165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS80799A CS241471B2 (cs)	1979-02-07	1980-02-06	Způsob výroby pyrimido-2-benzazepinů

Country Status (3)

Country	Link
AR (1)	AR229881A1 (da)
CS (1)	CS241471B2 (da)
DK (1)	DK49880A (da)

1980
- 1980-02-05 DK DK49880A patent/DK49880A/da not_active Application Discontinuation
- 1980-02-06 CS CS80799A patent/CS241471B2/cs unknown
- 1980-02-06 AR AR279890A patent/AR229881A1/es active

Also Published As

Publication number	Publication date
DK49880A (da)	1980-08-08
CS79980A2 (en)	1985-07-16
AR229881A1 (es)	1983-12-30

Publication	Publication Date	Title
US3211731A (en)	1965-10-12	Pyrazolo-pyrimidines and process for preparing same
US3384635A (en)	1968-05-21	1, 4-benzodiazepine derivatives
FI68050C (fi)	1985-07-10	Foerfarande foer framstaellning av farmaceutiskt anvaendbara 2-asylaminometyl-1h-2,3-dihydro-1,4-benzodiazepiner
PT93823B (pt)	1996-09-30	Processo para a preparacao de derivados de pirimidina e de composicoes farmaceuticas que os contem
NZ251804A (en)	1997-06-24	Aromatic quinazoline derivatives and medicaments
SK56195A3 (en)	1996-05-08	Pyrrolopyrimidine derivatives with pharmacologic effeciency
US4772607A (en)	1988-09-20	Dialkenyl derivatives of xanthine, pharmaceutical compositions and methods of use therefor
EP0150469B1 (en)	1988-06-15	Thieno(2,3-d)pyrimidine derivatives and salts thereof
US5574039A (en)	1996-11-12	Antiproliferative compounds having nitrogen-containing tricyclic ring systems and phenyl substituents
DE69619259T2 (de)	2002-09-19	Amidin- und isothioharnstoffderivate als inhibitoren der stickstoffoxid-synthase
US3818003A (en)	1974-06-18	Tricyclic benzodiazepines
DE3004381A1 (de)	1980-09-04	Benzazepin-derivate
FI77456B (fi)	1988-11-30	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-/2-/4-(2-metoxifenyl) -1-piperazinyl/etyl/-2,4-(1h,3h)-kinazolindionderivat.
HU186975B (en)	1985-10-28	Process for preparing new triazolo-quinazolone derivatives
CS242894B2 (en)	1986-05-15	Method of compounds production with a diazotized heterocyclic core
CA1136136A (en)	1982-11-23	Triazinones
US4612312A (en)	1986-09-16	Glutarimide antianxiety and antihypertensive agents
US4608375A (en)	1986-08-26	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
HU188475B (en)	1986-04-28	Process for producing benzothiopyrano-pyridinones
CS241471B2 (cs)	1986-03-13	Způsob výroby pyrimido-2-benzazepinů
DE69121894T2 (de)	1997-02-06	Heterocyclische verbindungen, herstellung und verwendung
US4009175A (en)	1977-02-22	1-[(Aminooxy)-methyl]-6-substituted-4H-s-triazolo[4,3-a][1,4] benzodiazepines
SK283489B6 (sk)	2003-08-05	Piperazinylalkyltiopyrimidínové deriváty, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie
Rostom et al.	2003	Synthesis and in vitro anti-HIV screening of certain 2-(benzoxazol-2-ylamino)-3H-4-oxopyrimidines
US3882112A (en)	1975-05-06	7-Phenyl-3-{8 2-(dialkylamino)-alkyl{9 -3,4-dihydroas-triazino{8 4,3-a{9 {8 1,4{9 benzodiazepin-2(1h)-ones