NO781053L - Kinazolinderivater. - Google Patents

Kinazolinderivater.

Info

Publication number: NO781053L
Authority: NO; Norway
Prior art keywords: formula; pyrido; quinazoline; oxo; stated
Prior art date: 1977-03-24

Application number

NO781053A

Other languages

English (en)

Norwegian (no)

Inventor

Richard Wightman Kierstead

Jefferson Wright Tilley

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.)

1977-03-24

Filing date

1978-03-22

Publication date

1978-09-26

1978-03-22 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1978-09-26 Publication of NO781053L publication Critical patent/NO781053L/no

Links

150000001875 compounds Chemical class 0.000 claims description 91
125000000217 alkyl group Chemical group 0.000 claims description 56
238000000034 method Methods 0.000 claims description 50
238000002360 preparation method Methods 0.000 claims description 47
-1 cyano, 5-tetrazolyl Chemical group 0.000 claims description 46
239000007787 solid Substances 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 43
125000003545 alkoxy group Chemical group 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
125000004414 alkyl thio group Chemical group 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 18
UPGZAERNNNZSPM-UHFFFAOYSA-N quinazoline-8-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CC=CC2=C1 UPGZAERNNNZSPM-UHFFFAOYSA-N 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
PNVRFQIVLRDFMU-UHFFFAOYSA-N 2-methoxy-11-oxopyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C(O)=O)=CN2C(=O)C3=CC(OC)=CC=C3N=C21 PNVRFQIVLRDFMU-UHFFFAOYSA-N 0.000 claims description 11
QBEIZCZOJLXENV-UHFFFAOYSA-N 9h-pyrido[2,1-b]quinazoline Chemical class C1=CC=CC2=CN3CC=CC=C3N=C21 QBEIZCZOJLXENV-UHFFFAOYSA-N 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 8
239000002585 base Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
230000003266 anti-allergic effect Effects 0.000 claims description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
150000005748 halopyridines Chemical class 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
PYBKWRFBLKRVDV-UHFFFAOYSA-N 11-oxo-2-propan-2-yloxypyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C(O)=O)=CN2C(=O)C3=CC(OC(C)C)=CC=C3N=C21 PYBKWRFBLKRVDV-UHFFFAOYSA-N 0.000 claims description 4
WOWXQGVIYOJJJX-UHFFFAOYSA-N 11-oxo-2-propan-2-ylpyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C(O)=O)=CN2C(=O)C3=CC(C(C)C)=CC=C3N=C21 WOWXQGVIYOJJJX-UHFFFAOYSA-N 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
STYICFCLHAZONT-UHFFFAOYSA-N 2-cyclopropyl-11-oxopyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=C2C(=O)N3C=C(C(=O)O)C=CC3=NC2=CC=C1C1CC1 STYICFCLHAZONT-UHFFFAOYSA-N 0.000 claims description 4
ULOYTSDTMQNZNZ-UHFFFAOYSA-N 2-methylsulfanyl-11-oxopyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C(O)=O)=CN2C(=O)C3=CC(SC)=CC=C3N=C21 ULOYTSDTMQNZNZ-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
150000007530 organic bases Chemical group 0.000 claims description 4
LPCONMIBYTZEGU-UHFFFAOYSA-N 2-(2-methoxy-11-oxopyrido[2,1-b]quinazolin-8-yl)acetic acid Chemical compound C1=CC(CC(O)=O)=CN2C(=O)C3=CC(OC)=CC=C3N=C21 LPCONMIBYTZEGU-UHFFFAOYSA-N 0.000 claims description 3
DJQMJLODWZIUAH-UHFFFAOYSA-N 2-(diethylamino)ethyl 11-oxo-2-propan-2-ylpyrido[2,1-b]quinazoline-8-carboxylate Chemical compound C1=C(C(C)C)C=C2C(=O)N(C=C(C(=O)OCCN(CC)CC)C=C3)C3=NC2=C1 DJQMJLODWZIUAH-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical group CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000006136 alcoholysis reaction Methods 0.000 claims description 2
238000005915 ammonolysis reaction Methods 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
LYLILIWTSDTYFW-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-cyclopropyl-11-oxo-1H-pyrido[2,1-b]quinazoline-2-carboxylate Chemical compound C1C(C(N2C=CC=CC2=N2)=O)=C2C=CC1(C(=O)OCCN(CC)CC)C1CC1 LYLILIWTSDTYFW-UHFFFAOYSA-N 0.000 claims 2
OUNMDQGVAGJXJI-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methoxy-11-oxopyrido[2,1-b]quinazoline-8-carboxylate Chemical compound C1=C(OC)C=C2C(=O)N(C=C(C(=O)OCCN(CC)CC)C=C3)C3=NC2=C1 OUNMDQGVAGJXJI-UHFFFAOYSA-N 0.000 claims 2
KRFHRAAUBLAPSM-UHFFFAOYSA-N 4-methoxy-11-oxopyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C2=C1C(OC)=CC=C2 KRFHRAAUBLAPSM-UHFFFAOYSA-N 0.000 claims 2
PNKHNBKVYZXUMH-UHFFFAOYSA-N 2,4-dimethoxy-11-oxopyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C(O)=O)=CN2C(=O)C3=CC(OC)=CC(OC)=C3N=C21 PNKHNBKVYZXUMH-UHFFFAOYSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 60
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
238000001816 cooling Methods 0.000 description 25
229960000583 acetic acid Drugs 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 23
239000000725 suspension Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
229910052786 argon Inorganic materials 0.000 description 17
239000003921 oil Substances 0.000 description 17
235000019198 oils Nutrition 0.000 description 17
239000000047 product Substances 0.000 description 16
UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 13
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000012043 crude product Substances 0.000 description 11
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
238000010992 reflux Methods 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
UMKSAURFQFUULT-UHFFFAOYSA-N 2-Amino-5-methoxybenzoic acid Chemical compound COC1=CC=C(N)C(C(O)=O)=C1 UMKSAURFQFUULT-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000004821 distillation Methods 0.000 description 8
208000009079 Bronchial Spasm Diseases 0.000 description 7
208000014181 Bronchial disease Diseases 0.000 description 7
206010006482 Bronchospasm Diseases 0.000 description 7
239000000538 analytical sample Substances 0.000 description 7
239000013078 crystal Substances 0.000 description 7
PDGKZXSVTBEAFW-UHFFFAOYSA-N (6-chloropyridin-3-yl)methyl benzoate Chemical compound C1=NC(Cl)=CC=C1COC(=O)C1=CC=CC=C1 PDGKZXSVTBEAFW-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
QWNMKHLBVHTPFW-UHFFFAOYSA-N 2-amino-5-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=C(N)C(C(O)=O)=C1 QWNMKHLBVHTPFW-UHFFFAOYSA-N 0.000 description 5
150000001204 N-oxides Chemical class 0.000 description 5
241000700159 Rattus Species 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000000427 antigen Substances 0.000 description 5
102000036639 antigens Human genes 0.000 description 5
108091007433 antigens Proteins 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
238000003756 stirring Methods 0.000 description 5
LKWPCZDBLQUFJQ-UHFFFAOYSA-N 2-amino-5-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=C(N)C(C(O)=O)=C1 LKWPCZDBLQUFJQ-UHFFFAOYSA-N 0.000 description 4
RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 4
YCUBIGBFPFQZAU-UHFFFAOYSA-N 6-chloro-n-[2-(diethylamino)ethyl]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.CCN(CC)CCNC(=O)C1=CC=C(Cl)N=C1 YCUBIGBFPFQZAU-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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 4
229920000881 Modified starch Polymers 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000011282 treatment Methods 0.000 description 4
UERVAQKRBPRDJP-UHFFFAOYSA-N 2-amino-5-cyclopropylbenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1CC1 UERVAQKRBPRDJP-UHFFFAOYSA-N 0.000 description 3
BUHKQTKKZAXSMH-UHFFFAOYSA-N 5-hydroxy-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1[N+]([O-])=O BUHKQTKKZAXSMH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
XVUDRSZQKGTCPH-UHFFFAOYSA-N acetic acid;n,n-dimethylformamide Chemical compound CC(O)=O.CN(C)C=O XVUDRSZQKGTCPH-UHFFFAOYSA-N 0.000 description 3
RIEYKVLCMDCSJY-UHFFFAOYSA-N acetic acid;n,n-dimethylformamide;hydrate Chemical compound O.CC(O)=O.CN(C)C=O RIEYKVLCMDCSJY-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000002156 mixing Methods 0.000 description 3
YWDFEVSRIBDNQY-UHFFFAOYSA-N propan-2-yl 2-nitro-5-propan-2-yloxybenzoate Chemical compound CC(C)OC(=O)C1=CC(OC(C)C)=CC=C1[N+]([O-])=O YWDFEVSRIBDNQY-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 3
239000000523 sample Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
UXSNZYGTQTXRAD-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)N=C1 UXSNZYGTQTXRAD-UHFFFAOYSA-N 0.000 description 2
OIZVMXRXSQFFMQ-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 2-methoxy-11-oxopyrido[2,1-b]quinazoline-8-carboxylate Chemical compound C1=CC(C(=O)OCOC(=O)C(C)(C)C)=CN2C(=O)C3=CC(OC)=CC=C3N=C21 OIZVMXRXSQFFMQ-UHFFFAOYSA-N 0.000 description 2
XYHSEANJTLQCQL-UHFFFAOYSA-N 2-methoxy-11-oxopyrido[2,1-b]quinazoline-7-carboxylic acid Chemical compound C1=C(C(O)=O)C=CN2C(=O)C3=CC(OC)=CC=C3N=C21 XYHSEANJTLQCQL-UHFFFAOYSA-N 0.000 description 2
BZVMHJYYJKXSAS-UHFFFAOYSA-N 2-methoxy-11-oxopyrido[2,1-b]quinazoline-8-carbonitrile Chemical compound C1=CC(C#N)=CN2C(=O)C3=CC(OC)=CC=C3N=C21 BZVMHJYYJKXSAS-UHFFFAOYSA-N 0.000 description 2
CRXURRMYQKUFNV-UHFFFAOYSA-N 2-methoxy-11-oxopyrido[2,1-b]quinazoline-8-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC(C(O)=O)=CN2C(=O)C3=CC(OC)=CC=C3N=C21 CRXURRMYQKUFNV-UHFFFAOYSA-N 0.000 description 2
JWAVEEBWRNQONY-UHFFFAOYSA-N 2-methyl-11-oxopyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C(O)=O)=CN2C(=O)C3=CC(C)=CC=C3N=C21 JWAVEEBWRNQONY-UHFFFAOYSA-N 0.000 description 2
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
KDEGRRHCRBMOQN-UHFFFAOYSA-N acetic acid;methanol;hydrochloride Chemical compound Cl.OC.CC(O)=O KDEGRRHCRBMOQN-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000002052 anaphylactic effect Effects 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
230000002804 anti-anaphylactic effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000005333 aroyloxy group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
OXUVDEGTBOXDCT-UHFFFAOYSA-N benzoic acid;8-(hydroxymethyl)-2-propan-2-yloxypyrido[2,1-b]quinazolin-11-one Chemical compound OC(=O)C1=CC=CC=C1.C1=CC(CO)=CN2C(=O)C3=CC(OC(C)C)=CC=C3N=C21 OXUVDEGTBOXDCT-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
235000012241 calcium silicate Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
229960002327 chloral hydrate Drugs 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical group 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
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
ZVVRNGUAGINQLA-UHFFFAOYSA-N methyl 2-aminobenzoate;hydrochloride Chemical class Cl.COC(=O)C1=CC=CC=C1N ZVVRNGUAGINQLA-UHFFFAOYSA-N 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
RRLNUWRVTRDWIX-UHFFFAOYSA-N n-(4-cyclopropylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1CC1 RRLNUWRVTRDWIX-UHFFFAOYSA-N 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
QMYZFEFSEQOZPW-UHFFFAOYSA-N o-methyl 2-amino-5-methylbenzenecarbothioate Chemical compound COC(=S)C1=CC(C)=CC=C1N QMYZFEFSEQOZPW-UHFFFAOYSA-N 0.000 description 1
HWOLJTHAQMRDQW-UHFFFAOYSA-N o-methyl 2-amino-5-methylbenzenecarbothioate;hydrochloride Chemical compound Cl.COC(=S)C1=CC(C)=CC=C1N HWOLJTHAQMRDQW-UHFFFAOYSA-N 0.000 description 1
MBJJMQNFXISCGG-UHFFFAOYSA-N o-methyl 5-methyl-2-nitrobenzenecarbothioate Chemical compound COC(=S)C1=CC(C)=CC=C1[N+]([O-])=O MBJJMQNFXISCGG-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
WWABBFPTGJZEDN-UHFFFAOYSA-N quinazoline-6-carboxylic acid Chemical compound N1=CN=CC2=CC(C(=O)O)=CC=C21 WWABBFPTGJZEDN-UHFFFAOYSA-N 0.000 description 1
GYBHRTQLUQOYID-UHFFFAOYSA-N quinazoline-8-carboxamide Chemical compound N1=CN=C2C(C(=O)N)=CC=CC2=C1 GYBHRTQLUQOYID-UHFFFAOYSA-N 0.000 description 1
150000003246 quinazolines Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
238000010626 work up procedure Methods 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
- 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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)

NO781053A 1977-03-24 1978-03-22 Kinazolinderivater. NO781053L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US78093977A	1977-03-24	1977-03-24
US87156478A	1978-01-23	1978-01-23

Publications (1)

Publication Number	Publication Date
NO781053L true NO781053L (no)	1978-09-26

Family

ID=27119777

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO781053A NO781053L (no)	1977-03-24	1978-03-22	Kinazolinderivater.
NO781051A NO781051L (no)	1977-03-24	1978-03-22	Kinazolinderivater.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO781051A NO781051L (no)	1977-03-24	1978-03-22	Kinazolinderivater.

Country Status (23)

Country	Link
JP (2)	JPS53119896A (el)
AR (3)	AR218060A1 (el)
AT (2)	AT367050B (el)
AU (2)	AU521352B2 (el)
DE (2)	DE2812586A1 (el)
DK (2)	DK128878A (el)
ES (13)	ES468126A1 (el)
FI (2)	FI780918A (el)
FR (2)	FR2384770A1 (el)
GB (2)	GB1601991A (el)
GR (2)	GR73170B (el)
HU (1)	HU180782B (el)
IE (1)	IE46505B1 (el)
IL (2)	IL54326A (el)
IT (2)	IT1093710B (el)
LU (2)	LU79290A1 (el)
MC (2)	MC1186A1 (el)
NL (2)	NL7803122A (el)
NO (2)	NO781053L (el)
NZ (2)	NZ186760A (el)
PH (2)	PH13915A (el)
PT (2)	PT67821B (el)
SE (2)	SE7803418L (el)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2557425C2 (de) *	1975-12-19	1987-03-19	C.H. Boehringer Sohn, 6507 Ingelheim	11-Oxo-11-H-pyrido[2,1-b]-chinazolin-2-carbonsäure und ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel
DE2845766A1 (de) *	1978-10-18	1980-04-30	Schering Ag	Pyrido eckige klammer auf 2,1-b eckige klammer zu -chinazolinon-derivate, ihre herstellung und verwendung
US4395549A (en)	1981-10-02	1983-07-26	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.	6-Hydrazono-pyrido[2,1-b] quinazoline-11 ones
ES511866A0 (es) *	1982-04-30	1983-06-01	Lafarquim	"procedimiento de obtencion de 2-isopropil pirido (2-1-b) quinazolinas y sus sales no toxicas con actividad antianafilactica".
US4551460A (en) *	1982-05-10	1985-11-05	Hoffmann-La Roche Inc.	Pyrido[2,1-b]quinazoline derivatives useful as agents for treatment of allergic conditions and vascular disorders involving thrombosis
DE3300477A1 (de) *	1983-01-08	1984-07-12	Boehringer Ingelheim KG, 6507 Ingelheim	Neue heterocyclische verbindungen, ihre herstellung und verwendung
JPS62238264A (ja) *	1986-04-04	1987-10-19	Nippon Tokushu Noyaku Seizo Kk	２−ハロ−５−アセチルピリジン

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US4012387A (en) *	1975-09-18	1977-03-15	Warner-Lambert Company	Benzo-[g]pyrido[2,1-b]quinazolinones
US4033961A (en) *	1975-10-07	1977-07-05	Warner-Lambert Company	Pyrido[2-1-b]quinazolin-ones and their methods of preparation

1978
- 1978-03-22 LU LU79290A patent/LU79290A1/de unknown
- 1978-03-22 NZ NZ186760A patent/NZ186760A/xx unknown
- 1978-03-22 ES ES468126A patent/ES468126A1/es not_active Expired
- 1978-03-22 NL NL7803122A patent/NL7803122A/xx not_active Application Discontinuation
- 1978-03-22 NZ NZ186759A patent/NZ186759A/xx unknown
- 1978-03-22 NO NO781053A patent/NO781053L/no unknown
- 1978-03-22 HU HU78HO2058A patent/HU180782B/hu unknown
- 1978-03-22 NL NL7803112A patent/NL7803112A/xx not_active Application Discontinuation
- 1978-03-22 FR FR7808316A patent/FR2384770A1/fr active Granted
- 1978-03-22 PH PH20917A patent/PH13915A/en unknown
- 1978-03-22 LU LU79293A patent/LU79293A1/de unknown
- 1978-03-22 DK DK128878A patent/DK128878A/da not_active Application Discontinuation
- 1978-03-22 FR FR7808317A patent/FR2384771A1/fr active Granted
- 1978-03-22 IL IL54326A patent/IL54326A/xx unknown
- 1978-03-22 DE DE19782812586 patent/DE2812586A1/de not_active Withdrawn
- 1978-03-22 PH PH20918A patent/PH14130A/en unknown
- 1978-03-22 DK DK132778A patent/DK132778A/da not_active IP Right Cessation
- 1978-03-22 IL IL54328A patent/IL54328A/xx unknown
- 1978-03-22 MC MC781292A patent/MC1186A1/xx unknown
- 1978-03-22 MC MC781291A patent/MC1185A1/xx unknown
- 1978-03-22 ES ES468127A patent/ES468127A1/es not_active Expired
- 1978-03-22 DE DE19782812585 patent/DE2812585A1/de not_active Withdrawn
- 1978-03-22 NO NO781051A patent/NO781051L/no unknown
- 1978-03-23 IT IT7821578A patent/IT1093710B/it active
- 1978-03-23 GB GB11705/78A patent/GB1601991A/en not_active Expired
- 1978-03-23 GB GB11704/78A patent/GB1601371A/en not_active Expired
- 1978-03-23 PT PT67821A patent/PT67821B/pt unknown
- 1978-03-23 SE SE7803418A patent/SE7803418L/xx unknown
- 1978-03-23 PT PT67820A patent/PT67820A/pt unknown
- 1978-03-23 SE SE7803419A patent/SE7803419L/xx unknown
- 1978-03-23 AU AU34474/78A patent/AU521352B2/en not_active Expired
- 1978-03-23 IE IE582/78A patent/IE46505B1/en unknown
- 1978-03-23 AT AT0210278A patent/AT367050B/de not_active IP Right Cessation
- 1978-03-23 GR GR55782A patent/GR73170B/el unknown
- 1978-03-23 AU AU34475/78A patent/AU521096B2/en not_active Expired
- 1978-03-23 GR GR55781A patent/GR72948B/el unknown
- 1978-03-23 FI FI780918A patent/FI780918A/fi not_active Application Discontinuation
- 1978-03-23 AT AT0210478A patent/AT367051B/de not_active IP Right Cessation
- 1978-03-23 FI FI780917A patent/FI780917A/fi not_active Application Discontinuation
- 1978-03-24 JP JP3320578A patent/JPS53119896A/ja active Pending
- 1978-03-24 IT IT21655/78A patent/IT1095493B/it active
- 1978-03-24 JP JP3400278A patent/JPS53119897A/ja active Pending
- 1978-03-27 AR AR271538A patent/AR218060A1/es active
- 1978-03-27 AR AR271537A patent/AR218480A1/es active
1979
- 1979-02-16 ES ES478332A patent/ES478332A1/es not_active Expired
- 1979-02-16 ES ES478325A patent/ES478325A1/es not_active Expired
- 1979-02-16 ES ES478326A patent/ES478326A1/es not_active Expired
- 1979-02-16 ES ES478323A patent/ES478323A1/es not_active Expired
- 1979-02-16 ES ES478333A patent/ES478333A1/es not_active Expired
- 1979-02-16 ES ES478330A patent/ES478330A1/es not_active Expired
- 1979-02-16 ES ES478329A patent/ES478329A1/es not_active Expired
- 1979-02-16 ES ES478328A patent/ES478328A1/es not_active Expired
- 1979-02-16 ES ES478331A patent/ES478331A1/es not_active Expired
- 1979-02-16 ES ES478324A patent/ES478324A1/es not_active Expired
- 1979-02-16 ES ES478327A patent/ES478327A1/es not_active Expired
- 1979-05-10 AR AR276467A patent/AR225415A1/es active

Also Published As

Publication number	Publication date
GR72948B (el)	1984-01-17
NZ186759A (en)	1981-03-16
PT67821B (en)	1980-03-04
NL7803122A (nl)	1978-09-26
FR2384771B1 (el)	1980-04-04
ES478324A1 (es)	1979-11-01
GR73170B (el)	1983-02-14
ES478325A1 (es)	1979-11-01
AU521096B2 (en)	1982-03-18
FR2384770B1 (el)	1980-10-24
ES478330A1 (es)	1979-11-01
GB1601991A (en)	1981-11-04
AT367050B (de)	1982-05-25
NO781051L (no)	1978-09-26
GB1601371A (en)	1981-10-28
AU521352B2 (en)	1982-04-01
IL54326A (en)	1982-04-30
AU3447578A (en)	1979-09-27
IL54326A0 (en)	1978-06-15
ES478323A1 (es)	1979-11-01
NZ186760A (en)	1981-03-16
PT67821A (en)	1978-04-01
AR218480A1 (es)	1980-06-13
ES478327A1 (es)	1979-11-01
PH14130A (en)	1981-02-26
AU3447478A (en)	1979-09-27
ES478332A1 (es)	1979-11-16
IT7821655A0 (it)	1978-03-24
PT67820A (en)	1978-04-01
IT7821578A0 (it)	1978-03-23
DK128878A (da)	1978-09-25
ES478329A1 (es)	1979-11-01
MC1185A1 (fr)	1978-12-22
DK132778A (da)	1978-09-25
IT1093710B (it)	1985-07-26
ES468126A1 (es)	1979-09-01
ES478333A1 (es)	1979-11-16
ES478331A1 (es)	1979-11-16
IL54328A0 (en)	1978-06-15
ES478326A1 (es)	1979-11-01
SE7803419L (sv)	1978-09-25
LU79293A1 (de)	1979-05-25
PH13915A (en)	1980-11-04
ATA210478A (de)	1981-10-15
JPS53119896A (en)	1978-10-19
IT1095493B (it)	1985-08-10
IE46505B1 (en)	1983-06-29
ES478328A1 (es)	1979-11-01
FI780918A (fi)	1978-09-25
MC1186A1 (fr)	1978-12-22
LU79290A1 (de)	1979-05-25
IE780582L (en)	1978-09-24
HU180782B (en)	1983-04-29
FR2384771A1 (fr)	1978-10-20
AR225415A1 (es)	1982-03-31
ATA210278A (de)	1981-10-15
SE7803418L (sv)	1978-09-25
AR218060A1 (es)	1980-05-15
AT367051B (de)	1982-05-25
DE2812586A1 (de)	1978-09-28
NL7803112A (nl)	1978-09-26
IL54328A (en)	1982-03-31
FR2384770A1 (fr)	1978-10-20
JPS53119897A (en)	1978-10-19
ES468127A1 (es)	1979-09-16
DE2812585A1 (de)	1978-09-28
FI780917A (fi)	1978-09-25

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