SE436883B - Pyrimido /1,2-a/ azepinderivat, forfarande for deras framstellning och farmaceutiskt preparat - Google Patents

Pyrimido /1,2-a/ azepinderivat, forfarande for deras framstellning och farmaceutiskt preparat

Info

Publication number: SE436883B
Authority: SE; Sweden
Prior art keywords: lower alkyl; general formula; pyrimido; hydrogen; compound
Prior art date: 1979-05-11

Application number

SE8003478A

Other languages

English (en)

Swedish (sv)

Other versions

SE8003478L (sv

Inventor

J Kokosi

I Hermecz

Z Meszaros

G Szasz

L Vasvari

A Horvath

T Breining

Original Assignee

Chinoin Gyogyszer Es 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.)

1979-05-11

Filing date

1980-05-08

Publication date

1985-01-28

1980-05-08 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1980-11-12 Publication of SE8003478L publication Critical patent/SE8003478L/xx

1985-01-28 Publication of SE436883B publication Critical patent/SE436883B/sv

Links

238000000034 method Methods 0.000 title claims description 8
239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
150000001538 azepines Chemical class 0.000 title claims 2
238000002360 preparation method Methods 0.000 title description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
150000002825 nitriles Chemical class 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
GTLJSJNKRLFVSJ-UHFFFAOYSA-N 3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical class N=C1CCCCCN1 GTLJSJNKRLFVSJ-UHFFFAOYSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
230000003257 anti-anginal effect Effects 0.000 claims description 3
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims description 3
OKANYBNORCUPKZ-UHFFFAOYSA-N ethyl 2-ethyl-3-oxobutanoate Chemical compound CCOC(=O)C(CC)C(C)=O OKANYBNORCUPKZ-UHFFFAOYSA-N 0.000 claims description 3
GWMGLJWGCQLFBK-UHFFFAOYSA-N 1h-pyrimido[1,2-a]azepin-2-one Chemical compound C1=CC=CN2C=CC(=O)NC2=C1 GWMGLJWGCQLFBK-UHFFFAOYSA-N 0.000 claims description 2
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
XWIUIRQSQROZGJ-UHFFFAOYSA-N ethyl 2-(2-formylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1C=O XWIUIRQSQROZGJ-UHFFFAOYSA-N 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
TWFWQBPKFXUCJF-UHFFFAOYSA-N 3h-pyrimido[1,2-a]azepin-4-one Chemical compound C1=CC=CN2C(=O)CC=NC2=C1 TWFWQBPKFXUCJF-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000001640 fractional crystallisation Methods 0.000 claims 1
238000007127 saponification reaction Methods 0.000 claims 1
239000000243 solution Substances 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
230000008018 melting Effects 0.000 description 11
238000002844 melting Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
BATMIEQLHWRSOU-UHFFFAOYSA-N ethyl 2-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepine-3-carboxylate Chemical compound C1CCCCC2=NC(=O)C(C(=O)OCC)=CN21 BATMIEQLHWRSOU-UHFFFAOYSA-N 0.000 description 5
FVZLXIARAAOVCZ-UHFFFAOYSA-N 1h-azepine-3-carboxylic acid Chemical compound OC(=O)C1=CNC=CC=C1 FVZLXIARAAOVCZ-UHFFFAOYSA-N 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 3
150000003857 carboxamides Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
MYFDRUDDHLKXHE-UHFFFAOYSA-N ethyl 4-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepine-3-carboxylate Chemical compound C1CCCCN2C(=O)C(C(=O)OCC)=CN=C21 MYFDRUDDHLKXHE-UHFFFAOYSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
-1 robromide Chemical compound 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
LEUMFSTVJGBXTL-UHFFFAOYSA-N 3-phenyl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-4-one Chemical compound C=1N=C2CCCCCN2C(=O)C=1C1=CC=CC=C1 LEUMFSTVJGBXTL-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000010453 quartz Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
AVAQZFUVMGMHSC-UHFFFAOYSA-N 2-cyano-3-ethoxyprop-2-enoic acid Chemical compound CCOC=C(C#N)C(O)=O AVAQZFUVMGMHSC-UHFFFAOYSA-N 0.000 description 1
DERAACKMMNJAFU-UHFFFAOYSA-N 2-ethoxy-1,3-dioxane-4,6-dione Chemical compound CCOC1OC(=O)CC(=O)O1 DERAACKMMNJAFU-UHFFFAOYSA-N 0.000 description 1
VXJCASDXQBLRNI-UHFFFAOYSA-N 2-ethyl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-4-one Chemical compound C(C)C=1N=C2N(CCCCC2)C(C1)=O VXJCASDXQBLRNI-UHFFFAOYSA-N 0.000 description 1
OPIOZHYBAWFMHX-UHFFFAOYSA-N 2-oxo-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepine-3-carbohydrazide Chemical compound O=C1N=C2N(CCCCC2)C=C1C(=O)NN OPIOZHYBAWFMHX-UHFFFAOYSA-N 0.000 description 1
UHXGKJKOBGPMIE-UHFFFAOYSA-N 2-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepine-3-carbonitrile Chemical compound C1CCCCN2C=C(C#N)C(=O)N=C21 UHXGKJKOBGPMIE-UHFFFAOYSA-N 0.000 description 1
SOAWFTPUJKSXDC-UHFFFAOYSA-N 2-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepine-3-carboxylic acid Chemical compound C1CCCCC2=NC(=O)C(C(=O)O)=CN21 SOAWFTPUJKSXDC-UHFFFAOYSA-N 0.000 description 1
ADLRXOVAMNULLA-UHFFFAOYSA-N 3,4,5,6-tetrahydro-2h-azepin-2-amine Chemical compound NC1CCCCC=N1 ADLRXOVAMNULLA-UHFFFAOYSA-N 0.000 description 1
ZPDCGNJMYKAWOB-UHFFFAOYSA-N 3-ethyl-2-methyl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-4-one Chemical compound C1CCCCN2C(=O)C(CC)=C(C)N=C21 ZPDCGNJMYKAWOB-UHFFFAOYSA-N 0.000 description 1
KJIYVLIKLRBGBU-UHFFFAOYSA-N 3-methyl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-4-one;hydrochloride Chemical compound Cl.C1CCCCN2C(=O)C(C)=CN=C21 KJIYVLIKLRBGBU-UHFFFAOYSA-N 0.000 description 1
WURIPXVKHXQECZ-UHFFFAOYSA-N 3-phenyl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-2-one Chemical compound O=C1N=C2CCCCCN2C=C1C1=CC=CC=C1 WURIPXVKHXQECZ-UHFFFAOYSA-N 0.000 description 1
IRIDIPVOTWFODI-UHFFFAOYSA-N 4-oxo-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepine-3-carbonitrile Chemical compound C1CCCCN2C(=O)C(C#N)=CN=C21 IRIDIPVOTWFODI-UHFFFAOYSA-N 0.000 description 1
COWHMHWSHQPEAB-UHFFFAOYSA-N 7-methyl-3,4,5,6-tetrahydro-2h-azepin-2-amine Chemical compound CC1=NC(N)CCCC1 COWHMHWSHQPEAB-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010052895 Coronary artery insufficiency Diseases 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
FFGASZNXDRJHAV-UHFFFAOYSA-N S(=O)(=O)(OC)[O-].[NH2+]1C=CC=CC=C1 Chemical compound S(=O)(=O)(OC)[O-].[NH2+]1C=CC=CC=C1 FFGASZNXDRJHAV-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000006399 behavior Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 description 1
VVCYNVCCODBCOE-UHFFFAOYSA-N ethyl 2-methyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)C=O VVCYNVCCODBCOE-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
239000002245 particle Substances 0.000 description 1
210000004197 pelvis Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Heart & Thoracic Surgery (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Hospice & Palliative Care (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SE8003478A 1979-05-11 1980-05-08 Pyrimido /1,2-a/ azepinderivat, forfarande for deras framstellning och farmaceutiskt preparat SE436883B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU79CI1931A HU177184B (en)	1979-05-11	1979-05-11	Process for producing 2,3- and 3,4-disubstituted-hexahydro-pyrimido-square bracket-1,2-a-square bracket closed-asepines

Publications (2)

Publication Number	Publication Date
SE8003478L SE8003478L (sv)	1980-11-12
SE436883B true SE436883B (sv)	1985-01-28

Family

ID=10994746

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8003478A SE436883B (sv)	1979-05-11	1980-05-08	Pyrimido /1,2-a/ azepinderivat, forfarande for deras framstellning och farmaceutiskt preparat

Country Status (27)

Country	Link
US (1)	US4404205A (fr)
JP (1)	JPS5618984A (fr)
AR (1)	AR228136A1 (fr)
AT (1)	AT390615B (fr)
AU (1)	AU541505B2 (fr)
BE (1)	BE883216A (fr)
CA (1)	CA1143729A (fr)
CH (1)	CH649552A5 (fr)
CS (1)	CS216529B2 (fr)
DD (1)	DD150611A5 (fr)
DE (1)	DE3017565A1 (fr)
DK (1)	DK152500C (fr)
ES (1)	ES8104294A1 (fr)
FI (1)	FI70217C (fr)
FR (2)	FR2456106A1 (fr)
GB (1)	GB2051047B (fr)
GR (1)	GR68520B (fr)
HU (1)	HU177184B (fr)
IL (1)	IL60026A (fr)
IT (1)	IT1147733B (fr)
LU (1)	LU82436A1 (fr)
NL (1)	NL8002683A (fr)
NO (1)	NO154427C (fr)
PL (1)	PL123691B1 (fr)
PT (1)	PT71212A (fr)
SE (1)	SE436883B (fr)
SU (1)	SU981319A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU191192B (en) *	1982-11-16	1987-01-28	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu	Process for producing new azepino /1,2-a/ pyrimidine derivatives of bronchodilating activity and acid additional salts thereof and pharmaceiutical compositions containing them
DE69630799T2 (de) *	1995-09-06	2004-08-12	Kowa Co., Ltd., Nagoya	Pyrimidinderivate
US11681227B2 (en) *	2019-02-25	2023-06-20	Alex P. G. Robinson	Enhanced EUV photoresist materials, formulations and processes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE451733C (de)	1923-07-21	1927-11-03	A E Tschitschibabin Dr	Verfahren zur Darstellung von dicyklischen und polycyklischen Verbindungen, die hydrierte oder nichthydrierte Imidazol- oder Pyrimidinkerne enthalten
US3002000A (en) *	1958-11-08	1961-09-26	Bayer Ag	1,2-alkylene-dihydropyrimidone-6, and 1,2-alkylene-imidazolinones-(5)
DE1670480C2 (de) *	1966-11-02	1983-06-01	Chinoin Gyógyszer és Vegyészeti Termékek Gyára R.T., 1045 Budapest	Pyrido[1,2-a]pyrimidinderivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende pharmazeutische Präparate
BE788601A (fr) *	1971-09-10	1973-03-08	Takeda Chemical Industries Ltd	Procede de preparation de derives de pyrimidine
HU167676B (fr) *	1972-11-29	1975-11-28

1979
- 1979-05-11 HU HU79CI1931A patent/HU177184B/hu not_active IP Right Cessation
1980
- 1980-05-03 GR GR61854A patent/GR68520B/el unknown
- 1980-05-08 IL IL60026A patent/IL60026A/xx unknown
- 1980-05-08 DE DE19803017565 patent/DE3017565A1/de not_active Withdrawn
- 1980-05-08 SU SU802921150A patent/SU981319A1/ru active
- 1980-05-08 CS CS803260A patent/CS216529B2/cs unknown
- 1980-05-08 SE SE8003478A patent/SE436883B/sv not_active IP Right Cessation
- 1980-05-09 US US06/148,234 patent/US4404205A/en not_active Expired - Lifetime
- 1980-05-09 BE BE0/200549A patent/BE883216A/fr not_active IP Right Cessation
- 1980-05-09 LU LU82436A patent/LU82436A1/de unknown
- 1980-05-09 DK DK204780A patent/DK152500C/da not_active IP Right Cessation
- 1980-05-09 AU AU58277/80A patent/AU541505B2/en not_active Ceased
- 1980-05-09 IT IT67722/80A patent/IT1147733B/it active
- 1980-05-09 DD DD80220985A patent/DD150611A5/de not_active IP Right Cessation
- 1980-05-09 CH CH3662/80A patent/CH649552A5/de not_active IP Right Cessation
- 1980-05-09 FR FR8010479A patent/FR2456106A1/fr active Granted
- 1980-05-09 CA CA000351665A patent/CA1143729A/fr not_active Expired
- 1980-05-09 GB GB8015418A patent/GB2051047B/en not_active Expired
- 1980-05-09 AT AT0247380A patent/AT390615B/de not_active IP Right Cessation
- 1980-05-09 AR AR280968A patent/AR228136A1/es active
- 1980-05-09 JP JP6161580A patent/JPS5618984A/ja active Pending
- 1980-05-09 PT PT71212A patent/PT71212A/pt unknown
- 1980-05-09 NO NO801377A patent/NO154427C/no unknown
- 1980-05-09 ES ES491360A patent/ES8104294A1/es not_active Expired
- 1980-05-09 FI FI801514A patent/FI70217C/fi not_active IP Right Cessation
- 1980-05-09 NL NL8002683A patent/NL8002683A/nl not_active Application Discontinuation
- 1980-05-10 PL PL1980224165A patent/PL123691B1/pl unknown
1981
- 1981-04-08 FR FR8107052A patent/FR2480602A1/fr active Granted

Also Published As

Publication number	Publication date
SU981319A1 (ru)	1982-12-15
IL60026A0 (en)	1980-07-31
DE3017565A1 (de)	1981-04-09
IT1147733B (it)	1986-11-26
PL224165A1 (fr)	1981-02-13
DK152500C (da)	1988-08-08
FR2456106B1 (fr)	1984-01-20
HU177184B (en)	1981-08-28
DD150611A5 (de)	1981-09-09
SE8003478L (sv)	1980-11-12
GB2051047B (en)	1983-09-14
PT71212A (en)	1980-06-01
FI801514A7 (fi)	1980-11-12
NL8002683A (nl)	1980-11-13
JPS5618984A (en)	1981-02-23
DK152500B (da)	1988-03-07
PL123691B1 (en)	1982-11-30
FR2480602B1 (fr)	1984-03-09
CA1143729A (fr)	1983-03-29
GR68520B (fr)	1982-01-11
FI70217C (fi)	1986-09-15
ES491360A0 (es)	1981-04-01
FR2456106A1 (fr)	1980-12-05
AR228136A1 (es)	1983-01-31
FI70217B (fi)	1986-02-28
AT390615B (de)	1990-06-11
US4404205A (en)	1983-09-13
DK204780A (da)	1980-11-12
BE883216A (fr)	1980-09-01
IT8067722A0 (it)	1980-05-09
NO801377L (no)	1980-11-12
CS216529B2 (en)	1982-11-26
AU5827780A (en)	1980-11-13
ES8104294A1 (es)	1981-04-01
NO154427C (no)	1986-09-17
AU541505B2 (en)	1985-01-10
IL60026A (en)	1984-02-29
ATA247380A (de)	1989-11-15
FR2480602A1 (fr)	1981-10-23
GB2051047A (en)	1981-01-14
CH649552A5 (de)	1985-05-31
LU82436A1 (de)	1980-07-31
NO154427B (no)	1986-06-09

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1995-01-31

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