NL8301505A - Gecondenseerde cycloalifatische derivaten van gesubstitueerde pyrido-1,2-a pyrimidinen, werkwijze voor de bereiding ervan en farmaceutische preparaten, die deze verbindingen bevatten. - Google Patents
Gecondenseerde cycloalifatische derivaten van gesubstitueerde pyrido-1,2-a pyrimidinen, werkwijze voor de bereiding ervan en farmaceutische preparaten, die deze verbindingen bevatten. Download PDFInfo
- Publication number
- NL8301505A NL8301505A NL8301505A NL8301505A NL8301505A NL 8301505 A NL8301505 A NL 8301505A NL 8301505 A NL8301505 A NL 8301505A NL 8301505 A NL8301505 A NL 8301505A NL 8301505 A NL8301505 A NL 8301505A
- Authority
- NL
- Netherlands
- Prior art keywords
- pyrido
- tetrahydro
- benzylidene
- oxo
- carboxylic acid
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 121
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- 150000003230 pyrimidines Chemical class 0.000 title 1
- -1 formyloxy group Chemical group 0.000 claims description 155
- 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 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 30
- LBMGFLVZIOZDHZ-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C1C=CN=C2C=CC(C(=O)O)=CN21 LBMGFLVZIOZDHZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000000460 chlorine Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- QHRQUMBXAYKEMS-UHFFFAOYSA-N 4-benzylidene-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=C1 QHRQUMBXAYKEMS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- IYPZGKADMRNZIS-UHFFFAOYSA-N 4-[(2-methylphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound CC1=CC=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 IYPZGKADMRNZIS-UHFFFAOYSA-N 0.000 claims description 4
- XGIGFMCNYPQGIC-UHFFFAOYSA-N 4-[(3-methoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1 XGIGFMCNYPQGIC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- BQDHJIPFPPPMPA-UHFFFAOYSA-N 11-oxo-4-(pyridin-3-ylmethylidene)-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CN=C1 BQDHJIPFPPPMPA-UHFFFAOYSA-N 0.000 claims description 3
- SCBJPAJKWKCWHJ-UHFFFAOYSA-N 3-(3-methoxy-benzylidene)-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CC2)=C1 SCBJPAJKWKCWHJ-UHFFFAOYSA-N 0.000 claims description 3
- LXCQKKWEFALERK-UHFFFAOYSA-N 4-[(2-methoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound COC1=CC=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 LXCQKKWEFALERK-UHFFFAOYSA-N 0.000 claims description 3
- KHVVMCYCHDANHJ-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=C(Cl)C(Cl)=C1 KHVVMCYCHDANHJ-UHFFFAOYSA-N 0.000 claims description 3
- LFQHFJNMSCYEPD-UHFFFAOYSA-N 4-[(3-chlorophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC(Cl)=C1 LFQHFJNMSCYEPD-UHFFFAOYSA-N 0.000 claims description 3
- VCHKEIMBROKRIH-UHFFFAOYSA-N 6-[(2,3-dimethoxyphenyl)methylidene]-2-oxo-1,8-diazatricyclo[7.4.0.03,7]trideca-3(7),8,10,12-tetraene-12-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CC2)=C1OC VCHKEIMBROKRIH-UHFFFAOYSA-N 0.000 claims description 3
- IYALGXCLEWIOEZ-UHFFFAOYSA-N 6-[(4-ethoxyphenyl)methylidene]-2-oxo-1,8-diazatricyclo[7.4.0.03,7]trideca-3(7),8,10,12-tetraene-12-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CC1 IYALGXCLEWIOEZ-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- FLESJLOTERFIMR-UHFFFAOYSA-N 4-[(2,3-dimethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1OC FLESJLOTERFIMR-UHFFFAOYSA-N 0.000 claims description 2
- PQQPWSKHNMAURX-UHFFFAOYSA-N 4-[(2,5-dimethylphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound CC1=CC=C(C)C(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1 PQQPWSKHNMAURX-UHFFFAOYSA-N 0.000 claims description 2
- HHYAJVADERPWHO-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 HHYAJVADERPWHO-UHFFFAOYSA-N 0.000 claims description 2
- FSADGQJCNUPMIA-UHFFFAOYSA-N 4-[(3-ethoxy-2-methoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound CCOC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1OC FSADGQJCNUPMIA-UHFFFAOYSA-N 0.000 claims description 2
- ACDGPSFNSGPUJE-UHFFFAOYSA-N 4-[(3-ethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound CCOC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1 ACDGPSFNSGPUJE-UHFFFAOYSA-N 0.000 claims description 2
- YPMRRQPOABVGQI-UHFFFAOYSA-N 4-[(4-ethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 YPMRRQPOABVGQI-UHFFFAOYSA-N 0.000 claims description 2
- OUTXTHGSFTULJT-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 OUTXTHGSFTULJT-UHFFFAOYSA-N 0.000 claims description 2
- KXHUNPZLNBSDEW-UHFFFAOYSA-N 4-[(4-methylphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 KXHUNPZLNBSDEW-UHFFFAOYSA-N 0.000 claims description 2
- APQMTCKETULICB-UHFFFAOYSA-N 4-benzylidene-8-oxo-2,9-diazatetracyclo[7.5.0.03,7.010,12]tetradeca-1,3(7),13-triene-12-carboxylic acid Chemical compound C1=CC2(C(=O)O)CC2N(C(C=2CC3)=O)C1=NC=2C3=CC1=CC=CC=C1 APQMTCKETULICB-UHFFFAOYSA-N 0.000 claims description 2
- LDNJLQJITIAGLI-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylidene]-2-oxo-1,8-diazatricyclo[7.4.0.03,7]trideca-3(7),8,10,12-tetraene-12-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CC1 LDNJLQJITIAGLI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- QLKLPUYYQQGZGG-UHFFFAOYSA-N 11-oxo-4-(pyridin-2-ylmethylidene)-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=N1 QLKLPUYYQQGZGG-UHFFFAOYSA-N 0.000 claims 1
- TZSLLMQNITWHRP-UHFFFAOYSA-N 3-(3-ethoxy-benzylidene)-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound CCOC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CC2)=C1 TZSLLMQNITWHRP-UHFFFAOYSA-N 0.000 claims 1
- MFVVEVAMGSGAOU-UHFFFAOYSA-N 3-benzylidene-7-methyl-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one Chemical compound C1CC=2C(=O)N3C=C(C)C=CC3=NC=2C1=CC1=CC=CC=C1 MFVVEVAMGSGAOU-UHFFFAOYSA-N 0.000 claims 1
- ZNHJBGDEZYIZGN-UHFFFAOYSA-N 4-[(2,6-dichlorophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=C(Cl)C=CC=C1Cl ZNHJBGDEZYIZGN-UHFFFAOYSA-N 0.000 claims 1
- MEBGECTZRYZCPD-UHFFFAOYSA-N 4-[(2-chlorophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=C1Cl MEBGECTZRYZCPD-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000002244 precipitate Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 159000000000 sodium salts Chemical class 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000005406 washing Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 8
- KRNUKLBBDTUZTB-UHFFFAOYSA-N 3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C1CC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=C1 KRNUKLBBDTUZTB-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 6
- 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 6
- 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 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 235000015424 sodium Nutrition 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000000026 anti-ulcerogenic effect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8212429 | 1982-04-29 | ||
| GB8212429 | 1982-04-29 | ||
| GB8309259 | 1983-04-06 | ||
| GB838309259A GB8309259D0 (en) | 1983-04-06 | 1983-04-06 | Condensed cycloaliphatic derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8301505A true NL8301505A (nl) | 1983-11-16 |
Family
ID=26282687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8301505A NL8301505A (nl) | 1982-04-29 | 1983-04-28 | Gecondenseerde cycloalifatische derivaten van gesubstitueerde pyrido-1,2-a pyrimidinen, werkwijze voor de bereiding ervan en farmaceutische preparaten, die deze verbindingen bevatten. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4521419A (enExample) |
| AT (1) | AT384808B (enExample) |
| AU (1) | AU557703B2 (enExample) |
| CA (1) | CA1192548A (enExample) |
| CH (1) | CH660485A5 (enExample) |
| CS (1) | CS233748B2 (enExample) |
| DE (1) | DE3315299A1 (enExample) |
| DK (1) | DK192683A (enExample) |
| ES (1) | ES8406476A1 (enExample) |
| FI (1) | FI74467C (enExample) |
| FR (1) | FR2526020B1 (enExample) |
| GR (1) | GR78546B (enExample) |
| HU (1) | HU188274B (enExample) |
| IL (1) | IL68505A (enExample) |
| IT (1) | IT1194215B (enExample) |
| LU (1) | LU84775A1 (enExample) |
| NL (1) | NL8301505A (enExample) |
| NO (1) | NO831503L (enExample) |
| NZ (1) | NZ204041A (enExample) |
| PH (1) | PH18388A (enExample) |
| PT (1) | PT76609B (enExample) |
| SE (1) | SE8302411L (enExample) |
| YU (1) | YU95583A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63183581A (ja) * | 1985-10-03 | 1988-07-28 | Tokyo Tanabe Co Ltd | ピリド〔１，２−ａ〕ピリミジン誘導体、その製造法及びそれを有効成分とするアレルギ−疾患治療薬 |
| CN112321465B (zh) * | 2019-07-18 | 2023-06-06 | 上海现代药物制剂工程研究中心有限公司 | 一种含苯基化合物、其中间体、制备方法及应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965100A (en) * | 1975-02-26 | 1976-06-22 | E. R. Squibb & Sons, Inc. | 2,3-Dihydrocyclopenta[d]pyrido[1,2-a]pyrimidin-10(1H)-one and its derivatives |
| US3935197A (en) * | 1975-05-16 | 1976-01-27 | E. R. Squibb & Sons, Inc. | 2-Styryl-4H-pyrido(1,2-a)pyrimidin-4-ones |
| US4033961A (en) * | 1975-10-07 | 1977-07-05 | Warner-Lambert Company | Pyrido[2-1-b]quinazolin-ones and their methods of preparation |
| 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 |
| HU174693B (hu) * | 1976-02-12 | 1980-03-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija kondensirovannykh proizvodnykh pirimidina |
| US4066767A (en) * | 1976-11-01 | 1978-01-03 | Warner-Lambert Company | 8-(1H-Tetrazol-5-yl)-11H-pyrido[2,1-b]quinazolin-11-ones and method of treating bronchial asthma using them |
| HU182009B (en) * | 1977-08-19 | 1983-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted pirido-square bracket-1,2-a-square bracket closed-pyrimidines, pyrrolo-square bracket-1,2-a-square bracket closed-pyrimidines |
| AU527931B2 (en) * | 1979-05-08 | 1983-03-31 | Farmitalia Carlo Erba S.P.A. | Substituted pyrido(1,2-a)pyrimidines |
| AT377586B (de) * | 1981-06-30 | 1985-04-10 | Erba Farmitalia | Verfahren zur herstellung von substituierten pyrrolo-(2,1-b)-chinazolinen und pyrido(2,1-b)chinazolinen |
-
1983
- 1983-04-22 ES ES521739A patent/ES8406476A1/es not_active Expired
- 1983-04-26 FI FI831426A patent/FI74467C/fi not_active IP Right Cessation
- 1983-04-26 IT IT20779/83A patent/IT1194215B/it active
- 1983-04-26 GR GR71210A patent/GR78546B/el unknown
- 1983-04-27 YU YU00955/83A patent/YU95583A/xx unknown
- 1983-04-27 HU HU831451A patent/HU188274B/hu not_active IP Right Cessation
- 1983-04-27 AU AU13991/83A patent/AU557703B2/en not_active Ceased
- 1983-04-27 LU LU84775A patent/LU84775A1/fr unknown
- 1983-04-27 DE DE19833315299 patent/DE3315299A1/de not_active Withdrawn
- 1983-04-27 IL IL68505A patent/IL68505A/xx unknown
- 1983-04-27 US US06/489,057 patent/US4521419A/en not_active Expired - Fee Related
- 1983-04-27 PH PH28824A patent/PH18388A/en unknown
- 1983-04-28 CS CS833005A patent/CS233748B2/cs unknown
- 1983-04-28 CH CH2286/83A patent/CH660485A5/de not_active IP Right Cessation
- 1983-04-28 FR FR8307052A patent/FR2526020B1/fr not_active Expired
- 1983-04-28 AT AT0154883A patent/AT384808B/de not_active IP Right Cessation
- 1983-04-28 SE SE8302411A patent/SE8302411L/xx not_active Application Discontinuation
- 1983-04-28 DK DK192683A patent/DK192683A/da not_active Application Discontinuation
- 1983-04-28 NO NO831503A patent/NO831503L/no unknown
- 1983-04-28 NL NL8301505A patent/NL8301505A/nl not_active Application Discontinuation
- 1983-04-28 CA CA000426896A patent/CA1192548A/en not_active Expired
- 1983-04-28 PT PT76609A patent/PT76609B/pt unknown
- 1983-04-28 NZ NZ204041A patent/NZ204041A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2526020B1 (fr) | 1986-03-21 |
| SE8302411L (sv) | 1983-10-30 |
| LU84775A1 (fr) | 1983-11-17 |
| PH18388A (en) | 1985-06-19 |
| US4521419A (en) | 1985-06-04 |
| NZ204041A (en) | 1985-02-28 |
| IL68505A0 (en) | 1983-07-31 |
| AT384808B (de) | 1988-01-11 |
| DK192683A (da) | 1983-10-30 |
| ES521739A0 (es) | 1984-07-01 |
| GR78546B (enExample) | 1984-09-27 |
| PT76609B (en) | 1986-01-17 |
| FI831426A0 (fi) | 1983-04-26 |
| ATA154883A (de) | 1987-06-15 |
| FI74467B (fi) | 1987-10-30 |
| FI831426L (fi) | 1983-10-30 |
| DK192683D0 (da) | 1983-04-28 |
| IT1194215B (it) | 1988-09-14 |
| FR2526020A1 (fr) | 1983-11-04 |
| IT8320779A0 (it) | 1983-04-26 |
| HU188274B (en) | 1986-03-28 |
| NO831503L (no) | 1983-10-31 |
| CH660485A5 (de) | 1987-04-30 |
| DE3315299A1 (de) | 1983-11-03 |
| FI74467C (fi) | 1988-02-08 |
| YU95583A (en) | 1986-12-31 |
| ES8406476A1 (es) | 1984-07-01 |
| CS233748B2 (en) | 1985-03-14 |
| IT8320779A1 (it) | 1984-10-26 |
| IL68505A (en) | 1986-01-31 |
| CA1192548A (en) | 1985-08-27 |
| SE8302411D0 (sv) | 1983-04-28 |
| PT76609A (en) | 1983-05-01 |
| AU1399183A (en) | 1983-11-03 |
| AU557703B2 (en) | 1987-01-08 |
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| JPH0122276B2 (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BV | The patent application has lapsed |