FR2475548A1 - Nouveaux derives de quinazoline, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux derives de quinazoline, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2475548A1 FR2475548A1 FR8102821A FR8102821A FR2475548A1 FR 2475548 A1 FR2475548 A1 FR 2475548A1 FR 8102821 A FR8102821 A FR 8102821A FR 8102821 A FR8102821 A FR 8102821A FR 2475548 A1 FR2475548 A1 FR 2475548A1
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- Prior art keywords
- amino
- group
- dimethoxy
- formula
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- Prior art date
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title claims description 44
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- NRQJIAVOKMKUOR-UHFFFAOYSA-N 2-piperazin-1-ylquinazoline Chemical class C1CNCCN1C1=NC=C(C=CC=C2)C2=N1 NRQJIAVOKMKUOR-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 claims description 198
- 150000001875 compounds Chemical class 0.000 claims description 176
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 35
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 6
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229940075559 piperine Drugs 0.000 claims description 5
- 150000003246 quinazolines Chemical class 0.000 claims description 5
- 101150035983 str1 gene Proteins 0.000 claims description 5
- 208000001953 Hypotension Diseases 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 125000001931 aliphatic 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
- 230000001077 hypotensive effect Effects 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000004050 homopiperazines Chemical class 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 230000001631 hypertensive effect Effects 0.000 claims description 3
- 208000021822 hypotensive Diseases 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 claims 2
- LTARAMBSPXICFP-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-2-phenylethanethione Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=S)CC1=CC=CC=C1 LTARAMBSPXICFP-UHFFFAOYSA-N 0.000 claims 1
- DCOWFYLEXDOVAM-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-3-phenylpropan-1-one Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)CCC1=CC=CC=C1 DCOWFYLEXDOVAM-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- AEKNYBWUEYNWMJ-QWOOXDRHSA-N Pramiconazole Chemical compound O=C1N(C(C)C)CCN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(CO3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 AEKNYBWUEYNWMJ-QWOOXDRHSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000005555 hypertensive agent Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 13
- QIPSSVPXEDZUJA-UHFFFAOYSA-N 2-(1,4-diazepan-1-yl)quinazoline Chemical compound C1CCNCCN1C1=NC=C(C=CC=C2)C2=N1 QIPSSVPXEDZUJA-UHFFFAOYSA-N 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 124
- 239000000203 mixture Substances 0.000 description 72
- 239000013078 crystal Substances 0.000 description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 62
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- 238000000921 elemental analysis Methods 0.000 description 39
- 238000001914 filtration Methods 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000000354 decomposition reaction Methods 0.000 description 25
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 22
- 229910001868 water Inorganic materials 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 21
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 20
- KIAYGSLXVNBIFE-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazoline Chemical compound N1=C(Cl)N=C2C=C(OC)C(OC)=CC2=C1 KIAYGSLXVNBIFE-UHFFFAOYSA-N 0.000 description 19
- 125000004193 piperazinyl group Chemical group 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 10
- APKHJGDGWQDBGM-UHFFFAOYSA-N 6,7-dimethoxy-2-piperazin-1-ylquinazolin-4-amine Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCNCC1 APKHJGDGWQDBGM-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 8
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 8
- 229960001289 prazosin Drugs 0.000 description 8
- RVZMPNMUBCAPQO-UHFFFAOYSA-N 2,4-dimethoxyquinazoline Chemical compound C1=CC=CC2=NC(OC)=NC(OC)=C21 RVZMPNMUBCAPQO-UHFFFAOYSA-N 0.000 description 7
- 206010020772 Hypertension Diseases 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- 125000004673 propylcarbonyl group Chemical group 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 4
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 3
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- ZIDNDHOWBISBIO-UHFFFAOYSA-N quinazoline;hydrate;hydrochloride Chemical compound O.Cl.N1=CN=CC2=CC=CC=C21 ZIDNDHOWBISBIO-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
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- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- BBUMHNGYUDGBRV-UHFFFAOYSA-N 2,4-dimethoxyquinazoline hydrate hydrochloride Chemical compound O.Cl.COC1=NC(=NC2=CC=CC=C12)OC BBUMHNGYUDGBRV-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- FYMQPWWNOCENRN-UHFFFAOYSA-N 6,7-dimethoxyquinazoline Chemical compound N1=CN=C2C=C(OC)C(OC)=CC2=C1 FYMQPWWNOCENRN-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 150000007530 organic bases Chemical class 0.000 description 2
- VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1677580A JPS56113770A (en) | 1980-02-13 | 1980-02-13 | Novel quinazoline derivative and its preparation |
| JP5275480A JPS56150072A (en) | 1980-04-21 | 1980-04-21 | Novel quinazoline derivative and its preparation |
| JP9610780A JPS5721385A (en) | 1980-07-14 | 1980-07-14 | Novel aminoquinazoline derivative and its preparation |
| JP9610680A JPS5721384A (en) | 1980-07-14 | 1980-07-14 | Novel aminoquinazoline derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2475548A1 true FR2475548A1 (fr) | 1981-08-14 |
| FR2475548B1 FR2475548B1 (forum.php) | 1983-06-24 |
Family
ID=27456647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8102821A Granted FR2475548A1 (fr) | 1980-02-13 | 1981-02-13 | Nouveaux derives de quinazoline, leur procede de preparation et leur application en therapeutique |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4426382A (forum.php) |
| CA (1) | CA1154765A (forum.php) |
| CH (1) | CH644857A5 (forum.php) |
| DE (1) | DE3105330A1 (forum.php) |
| ES (1) | ES8207169A1 (forum.php) |
| FR (1) | FR2475548A1 (forum.php) |
| GB (1) | GB2068961B (forum.php) |
| IT (1) | IT1172225B (forum.php) |
| NL (1) | NL191208C (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3419223A1 (de) * | 1983-06-01 | 1984-12-06 | SPOFA spojené továrny pro zdravotnickou výrobu, Prag/Praha | Substituierte acylpiperazinochinazoline, ein verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3346675A1 (de) * | 1983-12-23 | 1985-07-04 | Beiersdorf Ag, 2000 Hamburg | Substituierte 1-(4-amino-6,7-dialkoxy-chinazolinyl)-4- cyclohexenyl-derivate des piperazins und homopiperazins, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen und zwischenprodukte |
| JPH0647540B2 (ja) * | 1985-07-16 | 1994-06-22 | エーザイ株式会社 | 虚血性心疾患・不整脈治療・予防剤 |
| IT1270993B (it) * | 1994-03-18 | 1997-05-26 | Recordati Chem Pharm | Derivati chinzolilamminici attivi come alfa-antagonisti |
| TWI350168B (en) * | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| US8685961B2 (en) * | 2006-03-29 | 2014-04-01 | Merck Sharp & Dohme Corp. | Diazepan orexin receptor antagonists |
| PE20081229A1 (es) * | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| CA2687931C (en) | 2007-05-31 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists and uses thereof |
| WO2009143404A1 (en) * | 2008-05-23 | 2009-11-26 | Wyeth | Piperazine metabotropic glutamate receptor 5 (mglur5) negative allosteric modulators for anxiety/depression |
| WO2010070032A1 (en) | 2008-12-19 | 2010-06-24 | Boehringer Ingelheim International Gmbh | Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd |
| EP3091012B1 (en) | 2009-12-17 | 2018-04-11 | Centrexion Therapeutics Corporation | Ccr2 receptor antagonists and uses thereof |
| JP2013526507A (ja) | 2010-05-12 | 2013-06-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ｃｃｒ２受容体アンタゴニスト、その製造方法及び薬物としてのその使用 |
| US8946218B2 (en) | 2010-05-12 | 2015-02-03 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| US8841313B2 (en) | 2010-05-17 | 2014-09-23 | Boehringer Ingelheim International Gmbh | CCR2 antagonists and uses thereof |
| US9018212B2 (en) | 2010-05-25 | 2015-04-28 | Boehringer Ingelheim International Gmbh | Pyridazine carboxamides as CCR2 receptor antagonists |
| JP5721242B2 (ja) | 2010-06-01 | 2015-05-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ｃｃｒ２アンタゴニスト |
| EP2731941B1 (en) | 2011-07-15 | 2019-05-08 | Boehringer Ingelheim International GmbH | Novel and selective ccr2 antagonists |
| AU2013241854B2 (en) * | 2012-03-28 | 2017-11-02 | Intervet International B.V. | Heteroaryl compounds with cyclic bridging unit for use in the treatment helminth infection |
| CA2877526A1 (en) | 2012-06-20 | 2013-12-27 | Novartis Ag | Complement pathway modulators and uses thereof |
| US9732077B2 (en) | 2013-12-18 | 2017-08-15 | Merck Sharp & Dohme Corp. | Diazepane orexin receptor antagonists |
| MX383744B (es) | 2015-07-02 | 2025-03-14 | Centrexion Therapeutics Corp | Citrato de (4-((3r,4r)-3-metoxitetrahidro-piran-4-ilamino)piperidin-1-il) (5-metil-6-(((2r, 6s)-6-(p-tolil)tetrahidro-2h-piran-2-il) metilamino) pirimidin-4-il) metanona. |
| EP3648766A4 (en) * | 2017-07-06 | 2021-07-07 | Case Western Reserve University | PEPTIDIC AND SMALL MOLECULE AGONISTS OF WPHA AND THEIR USES |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2341576A1 (fr) * | 1976-02-18 | 1977-09-16 | Bristol Myers Co | 2-piperazinyl-6,7-dimethoxyquinazolines et leur application pharmacologique |
| GB2008106A (en) * | 1977-11-08 | 1979-05-31 | Mitsubishi Yuka Pharma | Quinazoline derivatives process for preparing the same and anthypertensive drugs containing the same |
| JPS5728576A (en) * | 1980-07-24 | 1982-02-16 | Toshiba Corp | Inverter device |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3511836A (en) * | 1967-12-13 | 1970-05-12 | Pfizer & Co C | 2,4,6,7-tetra substituted quinazolines |
| US3663706A (en) | 1969-09-29 | 1972-05-16 | Pfizer | Use of 2,4-diaminoquinazolines as hypotensive agents |
| JPS536156B2 (forum.php) * | 1972-10-30 | 1978-03-04 | ||
| US3935213A (en) | 1973-12-05 | 1976-01-27 | Pfizer Inc. | Process for hypotensive 4-amino-2-(piperazin-1-yl) quinazoline derivatives |
| US4001237A (en) * | 1976-02-18 | 1977-01-04 | Bristol-Myers Company | Oxazole, isoxazole, thiazole and isothiazole amides |
| US4287341A (en) | 1979-11-01 | 1981-09-01 | Pfizer Inc. | Alkoxy-substituted-6-chloro-quinazoline-2,4-diones |
-
1981
- 1981-02-11 US US06/233,679 patent/US4426382A/en not_active Expired - Fee Related
- 1981-02-11 GB GB8104185A patent/GB2068961B/en not_active Expired
- 1981-02-12 ES ES499377A patent/ES8207169A1/es not_active Expired
- 1981-02-12 CH CH94481A patent/CH644857A5/de not_active IP Right Cessation
- 1981-02-12 CA CA000370761A patent/CA1154765A/en not_active Expired
- 1981-02-13 FR FR8102821A patent/FR2475548A1/fr active Granted
- 1981-02-13 IT IT67213/81A patent/IT1172225B/it active
- 1981-02-13 NL NL8100726A patent/NL191208C/xx not_active IP Right Cessation
- 1981-02-13 DE DE19813105330 patent/DE3105330A1/de active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2341576A1 (fr) * | 1976-02-18 | 1977-09-16 | Bristol Myers Co | 2-piperazinyl-6,7-dimethoxyquinazolines et leur application pharmacologique |
| US4060615A (en) * | 1976-02-18 | 1977-11-29 | Mead Johnson & Company | 2-Piperazinyl-6,7-dimethoxyquinazolines |
| GB2008106A (en) * | 1977-11-08 | 1979-05-31 | Mitsubishi Yuka Pharma | Quinazoline derivatives process for preparing the same and anthypertensive drugs containing the same |
| JPS5728576A (en) * | 1980-07-24 | 1982-02-16 | Toshiba Corp | Inverter device |
Non-Patent Citations (1)
| Title |
|---|
| CA1977 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3419223A1 (de) * | 1983-06-01 | 1984-12-06 | SPOFA spojené továrny pro zdravotnickou výrobu, Prag/Praha | Substituierte acylpiperazinochinazoline, ein verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1154765A (en) | 1983-10-04 |
| IT8167213A0 (it) | 1981-02-13 |
| US4426382A (en) | 1984-01-17 |
| ES499377A0 (es) | 1982-09-01 |
| ES8207169A1 (es) | 1982-09-01 |
| NL8100726A (nl) | 1981-09-16 |
| FR2475548B1 (forum.php) | 1983-06-24 |
| DE3105330C2 (forum.php) | 1991-07-25 |
| GB2068961A (en) | 1981-08-19 |
| NL191208B (nl) | 1994-10-17 |
| NL191208C (nl) | 1995-03-16 |
| CH644857A5 (de) | 1984-08-31 |
| IT1172225B (it) | 1987-06-18 |
| DE3105330A1 (de) | 1981-12-17 |
| GB2068961B (en) | 1983-11-30 |
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