LU82434A1 - Procede de preparation de derives condenses de la pyrimidine,les sels,hydrates et isomeres de ceux-ci,certains representants de ces composes prepares et compositions pharmaceutiques contenant ceux-ci - Google Patents

Procede de preparation de derives condenses de la pyrimidine,les sels,hydrates et isomeres de ceux-ci,certains representants de ces composes prepares et compositions pharmaceutiques contenant ceux-ci Download PDF

Info

Publication number: LU82434A1
Authority: LU; Luxembourg
Prior art keywords: general formula; optionally substituted; group; compounds; optionally
Prior art date: 1979-05-11

Application number

LU82434A

Other languages

English (en)

French (fr)

Inventor

J Koekoesi

I Hermecz

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

1980-05-09

Publication date

1980-07-31

1980-05-09 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1980-07-31 Publication of LU82434A1 publication Critical patent/LU82434A1/fr

Links

150000001875 compounds Chemical class 0.000 title claims description 49
238000000034 method Methods 0.000 title claims description 22
150000003839 salts Chemical class 0.000 title claims description 16
150000004677 hydrates Chemical class 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 3
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 31
-1 organic acid nitrile Chemical class 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
239000011230 binding agent Substances 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000001589 carboacyl group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
125000003435 aroyl group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
125000005504 styryl group Chemical group 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
230000008018 melting Effects 0.000 description 10
238000002844 melting Methods 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000000950 dibromo group Chemical group Br* 0.000 description 8
239000000047 product Substances 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
230000003266 anti-allergic effect Effects 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
125000000168 pyrrolyl group Chemical group 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
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 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000005530 alkylenedioxy group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
125000005956 isoquinolyl group Chemical group 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
230000001766 physiological effect Effects 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000003373 pyrazinyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000005493 quinolyl group Chemical group 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
101000845012 Macrovipera lebetina Disintegrin lebein-1-alpha Proteins 0.000 description 1
101000845007 Macrovipera lebetina Disintegrin lebein-1-beta Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004902 Softening Agent Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
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230000001147 anti-toxic effect Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000005333 aroyloxy group Chemical group 0.000 description 1
125000002102 aryl alkyloxo group Chemical group 0.000 description 1
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125000004429 atom Chemical group 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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150000001735 carboxylic acids Chemical class 0.000 description 1
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238000005119 centrifugation Methods 0.000 description 1
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PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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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
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
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125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000002663 nebulization Methods 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008279 sol Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents

Landscapes

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

LU82434A 1979-05-11 1980-05-09 Procede de preparation de derives condenses de la pyrimidine,les sels,hydrates et isomeres de ceux-ci,certains representants de ces composes prepares et compositions pharmaceutiques contenant ceux-ci LU82434A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HUCI001933		1979-05-11
HU79CI1933A HU178452B (en)	1979-05-11	1979-05-11	Process for preparing 9-substituted amino-4-oxo-6,7-dihydro-4h-pyrido/1,2-a/pyrimidine derivatives

Publications (1)

Publication Number	Publication Date
LU82434A1 true LU82434A1 (fr)	1980-07-31

Family

ID=10994748

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82434A LU82434A1 (fr)	1979-05-11	1980-05-09	Procede de preparation de derives condenses de la pyrimidine,les sels,hydrates et isomeres de ceux-ci,certains representants de ces composes prepares et compositions pharmaceutiques contenant ceux-ci

Country Status (25)

Country	Link
US (1)	US4452982A (de)
JP (1)	JPS5618981A (de)
AT (1)	AT375938B (de)
AU (1)	AU546194B2 (de)
BE (1)	BE883218A (de)
CA (1)	CA1140124A (de)
CH (1)	CH653335A5 (de)
CS (1)	CS236752B2 (de)
DD (1)	DD150604A5 (de)
DE (1)	DE3017560A1 (de)
DK (1)	DK204980A (de)
ES (1)	ES491770A0 (de)
FI (1)	FI67549C (de)
FR (1)	FR2456100B1 (de)
GB (1)	GB2051784B (de)
HU (1)	HU178452B (de)
IL (1)	IL59968A (de)
IT (1)	IT8067718A0 (de)
LU (1)	LU82434A1 (de)
NL (1)	NL8002679A (de)
PL (1)	PL127344B1 (de)
PT (1)	PT71214A (de)
SE (1)	SE441748B (de)
SU (1)	SU1024007A3 (de)
YU (1)	YU122180A (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178453B (en) *	1979-05-11	1982-05-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing 9-hydrazino-4-oxo-6,7,8,9-tetrahydro-4h-p-pyrido-square bracket-1,2-a-square bracket closed-pyrimidine derivatives
US5252572A (en) *	1988-02-03	1993-10-12	Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt.	Pyridopyrimidine derivatives, pharmaceutical compositions containing them and process for preparing same
JP4747414B2 (ja) *	1999-11-09	2011-08-17	株式会社セガ	キーボード取付構造を有するビデオゲーム機
AU2003270783C1 (en) *	2002-09-20	2010-05-20	Merck Sharp & Dohme Corp.	Octahydro-2-H-naphtho[1,2-F] indole-4-carboxamide derivatives as selective glucocorticoid receptor modulators

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3141043A (en) *	1961-03-24	1964-07-14	Purdue Research Foundation	Cyclopentadienylimines, process for their production and condensation products thereof
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
HU180439B (en) *	1977-12-29	1983-03-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing 9-amino-pyrido-square bracket-1,2-a-square bracket closed-pyrimidine derivatives
HU178496B (en) *	1977-12-29	1982-05-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity

1979
- 1979-05-11 HU HU79CI1933A patent/HU178452B/hu unknown
1980
- 1980-05-01 IL IL59968A patent/IL59968A/xx unknown
- 1980-05-08 YU YU01221/80A patent/YU122180A/xx unknown
- 1980-05-08 CS CS803259A patent/CS236752B2/cs unknown
- 1980-05-08 SU SU802923101A patent/SU1024007A3/ru active
- 1980-05-08 SE SE8003480A patent/SE441748B/sv not_active IP Right Cessation
- 1980-05-08 DE DE19803017560 patent/DE3017560A1/de not_active Withdrawn
- 1980-05-09 AT AT0247780A patent/AT375938B/de not_active IP Right Cessation
- 1980-05-09 BE BE0/200551A patent/BE883218A/fr not_active IP Right Cessation
- 1980-05-09 DK DK204980A patent/DK204980A/da not_active Application Discontinuation
- 1980-05-09 LU LU82434A patent/LU82434A1/fr unknown
- 1980-05-09 US US06/148,238 patent/US4452982A/en not_active Expired - Lifetime
- 1980-05-09 PT PT71214A patent/PT71214A/pt unknown
- 1980-05-09 FR FR8010480A patent/FR2456100B1/fr not_active Expired
- 1980-05-09 FI FI801511A patent/FI67549C/fi not_active IP Right Cessation
- 1980-05-09 IT IT8067718A patent/IT8067718A0/it unknown
- 1980-05-09 AU AU58279/80A patent/AU546194B2/en not_active Ceased
- 1980-05-09 JP JP6161480A patent/JPS5618981A/ja active Pending
- 1980-05-09 GB GB8015470A patent/GB2051784B/en not_active Expired
- 1980-05-09 DD DD80220984A patent/DD150604A5/de unknown
- 1980-05-09 CH CH3664/80A patent/CH653335A5/de not_active IP Right Cessation
- 1980-05-09 CA CA000351664A patent/CA1140124A/en not_active Expired
- 1980-05-09 NL NL8002679A patent/NL8002679A/nl unknown
- 1980-05-10 PL PL1980224164A patent/PL127344B1/pl unknown
- 1980-05-10 ES ES491770A patent/ES491770A0/es active Granted

Also Published As

Publication number	Publication date
JPS5618981A (en)	1981-02-23
AU5827980A (en)	1980-11-13
ES8105004A1 (es)	1981-06-01
CA1140124A (en)	1983-01-25
CH653335A5 (de)	1985-12-31
SE441748B (sv)	1985-11-04
DE3017560A1 (de)	1980-11-13
US4452982A (en)	1984-06-05
YU122180A (en)	1983-02-28
HU178452B (en)	1982-05-28
IL59968A (en)	1984-05-31
PL127344B1 (en)	1983-10-31
PT71214A (en)	1980-06-01
ES491770A0 (es)	1981-06-01
GB2051784A (en)	1981-01-21
FI67549B (fi)	1984-12-31
DK204980A (da)	1980-11-12
FR2456100B1 (fr)	1985-08-09
AU546194B2 (en)	1985-08-22
BE883218A (fr)	1980-09-01
IL59968A0 (en)	1980-07-31
DD150604A5 (de)	1981-09-09
GB2051784B (en)	1983-03-02
FI67549C (fi)	1985-04-10
ATA247780A (de)	1984-02-15
IT8067718A0 (it)	1980-05-09
FR2456100A1 (fr)	1980-12-05
NL8002679A (nl)	1980-11-13
PL224164A1 (de)	1981-02-13
FI801511A7 (fi)	1980-11-12
AT375938B (de)	1984-09-25
CS236752B2 (en)	1985-05-15
SU1024007A3 (ru)	1983-06-15
SE8003480L (sv)	1980-11-12

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CZ151193A3 (en)	1994-03-16	2-substituted derivatives of quinolylmethoxyphenylacetic acid
EP0005091B1 (de)	1981-11-25	Monosubstituierte Piperazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
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