UA71976C2 - Bicyclic heterocycles and a medicament based thereon - Google Patents
Bicyclic heterocycles and a medicament based thereon Download PDFInfo
- Publication number
- UA71976C2 UA71976C2 UA2002010488A UA2002010488A UA71976C2 UA 71976 C2 UA71976 C2 UA 71976C2 UA 2002010488 A UA2002010488 A UA 2002010488A UA 2002010488 A UA2002010488 A UA 2002010488A UA 71976 C2 UA71976 C2 UA 71976C2
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- UA
- Ukraine
- Prior art keywords
- group
- amino
- alkyl
- substituted
- atom
- Prior art date
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- 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims abstract description 14
- 239000003814 drug Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 201000010099 disease Diseases 0.000 claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 210000002345 respiratory system Anatomy 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 210000004072 lung Anatomy 0.000 claims abstract description 4
- -1 hydroxy- Chemical class 0.000 claims description 250
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 162
- 125000000217 alkyl group Chemical group 0.000 claims description 123
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 58
- 239000012634 fragment Substances 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- 125000003277 amino group Chemical group 0.000 claims description 50
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 45
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 43
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 37
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 28
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 239000001301 oxygen Substances 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 27
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 239000011737 fluorine Substances 0.000 claims description 26
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims description 19
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 10
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- CWFLFGDTTKLLGN-UHFFFAOYSA-N 1-ethyl-1,4-diazepane Chemical group CCN1CCCNCC1 CWFLFGDTTKLLGN-UHFFFAOYSA-N 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- CHPRFKYDQRKRRK-UHFFFAOYSA-N 2-(methoxymethyl)pyrrolidine Chemical compound COCC1CCCN1 CHPRFKYDQRKRRK-UHFFFAOYSA-N 0.000 claims description 4
- ZEYSHALLPAKUHG-UHFFFAOYSA-N 4-methoxypiperidine Chemical compound COC1CCNCC1 ZEYSHALLPAKUHG-UHFFFAOYSA-N 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000005002 aryl methyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 4
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- FRXBWKFANYNBEO-UHFFFAOYSA-N 2-(ethoxymethyl)pyrrolidine Chemical compound CCOCC1CCCN1 FRXBWKFANYNBEO-UHFFFAOYSA-N 0.000 claims description 2
- OYHQAXYDSYSGEI-UHFFFAOYSA-N 4-ethoxypiperidine Chemical compound CCOC1CCNCC1 OYHQAXYDSYSGEI-UHFFFAOYSA-N 0.000 claims description 2
- YYBXNWIRMJXEQJ-UHFFFAOYSA-N 4-piperidin-4-ylmorpholine Chemical group C1CNCCC1N1CCOCC1 YYBXNWIRMJXEQJ-UHFFFAOYSA-N 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 210000000232 gallbladder Anatomy 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- BSAWOLABHUFGBJ-UHFFFAOYSA-N thiomorpholin-3-ol Chemical group OC1CSCCN1 BSAWOLABHUFGBJ-UHFFFAOYSA-N 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 229910018540 Si C Inorganic materials 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 210000003445 biliary tract Anatomy 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 1
- 229910010271 silicon carbide Inorganic materials 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract description 8
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 206010028980 Neoplasm Diseases 0.000 abstract description 4
- 235000005985 organic acids Nutrition 0.000 abstract description 4
- 230000019491 signal transduction Effects 0.000 abstract description 4
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 216
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 104
- 238000001819 mass spectrum Methods 0.000 description 91
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
- 239000000741 silica gel Substances 0.000 description 78
- 229910002027 silica gel Inorganic materials 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 235000019439 ethyl acetate Nutrition 0.000 description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 40
- 239000013543 active substance Substances 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 25
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 25
- 235000011114 ammonium hydroxide Nutrition 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 17
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
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- 239000002775 capsule Substances 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
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- 238000003756 stirring Methods 0.000 description 9
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 8
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 6
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1999128281 DE19928281A1 (de) | 1999-06-21 | 1999-06-21 | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| US14664499P | 1999-07-30 | 1999-07-30 | |
| DE2000123085 DE10023085A1 (de) | 2000-05-11 | 2000-05-11 | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| PCT/EP2000/005547 WO2000078735A1 (de) | 1999-06-21 | 2000-06-16 | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA71976C2 true UA71976C2 (en) | 2005-01-17 |
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|---|---|---|---|
| UA2002010488A UA71976C2 (en) | 1999-06-21 | 2000-06-16 | Bicyclic heterocycles and a medicament based thereon |
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| EP (2) | EP1731511B1 (bs) |
| JP (1) | JP3686610B2 (bs) |
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| CN (1) | CN1166645C (bs) |
| AU (1) | AU775285B2 (bs) |
| BG (1) | BG65890B1 (bs) |
| CA (1) | CA2375259C (bs) |
| CZ (1) | CZ302365B6 (bs) |
| DK (1) | DK1731511T3 (bs) |
| EA (1) | EA004981B1 (bs) |
| EE (1) | EE04748B1 (bs) |
| ES (1) | ES2552813T3 (bs) |
| HK (1) | HK1044769B (bs) |
| HU (1) | HUP0201900A3 (bs) |
| IL (2) | IL147133A0 (bs) |
| ME (1) | MEP45508A (bs) |
| MX (1) | MXPA01012899A (bs) |
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| NZ (1) | NZ516633A (bs) |
| PT (1) | PT1731511E (bs) |
| SK (1) | SK287010B6 (bs) |
| TR (1) | TR200103692T2 (bs) |
| UA (1) | UA71976C2 (bs) |
| WO (1) | WO2000078735A1 (bs) |
| YU (1) | YU90901A (bs) |
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2000
- 2000-06-16 ME MEP-455/08A patent/MEP45508A/bs unknown
- 2000-06-16 TR TR2001/03692T patent/TR200103692T2/xx unknown
- 2000-06-16 CA CA002375259A patent/CA2375259C/en not_active Expired - Lifetime
- 2000-06-16 YU YU90901A patent/YU90901A/sh unknown
- 2000-06-16 DK DK06116986.8T patent/DK1731511T3/en active
- 2000-06-16 ES ES06116986.8T patent/ES2552813T3/es not_active Expired - Lifetime
- 2000-06-16 JP JP2001504901A patent/JP3686610B2/ja not_active Expired - Lifetime
- 2000-06-16 CZ CZ20014497A patent/CZ302365B6/cs not_active IP Right Cessation
- 2000-06-16 PT PT61169868T patent/PT1731511E/pt unknown
- 2000-06-16 HU HU0201900A patent/HUP0201900A3/hu unknown
- 2000-06-16 MX MXPA01012899A patent/MXPA01012899A/es active IP Right Grant
- 2000-06-16 IL IL14713300A patent/IL147133A0/xx active IP Right Grant
- 2000-06-16 CN CNB00809201XA patent/CN1166645C/zh not_active Expired - Lifetime
- 2000-06-16 EE EEP200100695A patent/EE04748B1/xx not_active IP Right Cessation
- 2000-06-16 KR KR1020017016457A patent/KR100709909B1/ko active Protection Beyond IP Right Term
- 2000-06-16 EP EP06116986.8A patent/EP1731511B1/de not_active Expired - Lifetime
- 2000-06-16 NZ NZ516633A patent/NZ516633A/en not_active IP Right Cessation
- 2000-06-16 SK SK1845-2001A patent/SK287010B6/sk not_active IP Right Cessation
- 2000-06-16 WO PCT/EP2000/005547 patent/WO2000078735A1/de active IP Right Grant
- 2000-06-16 EA EA200200008A patent/EA004981B1/ru active Protection Beyond IP Right Term
- 2000-06-16 UA UA2002010488A patent/UA71976C2/uk unknown
- 2000-06-16 AU AU52214/00A patent/AU775285B2/en active Active
- 2000-06-16 EP EP00936888A patent/EP1194418A1/de not_active Ceased
-
2001
- 2001-12-07 BG BG106189A patent/BG65890B1/bg active Active
- 2001-12-10 US US10/016,280 patent/US7220750B2/en not_active Expired - Lifetime
- 2001-12-17 IL IL147133A patent/IL147133A/en unknown
- 2001-12-18 NO NO20016185A patent/NO322094B1/no not_active IP Right Cessation
-
2002
- 2002-08-27 HK HK02106291.1A patent/HK1044769B/zh not_active IP Right Cessation
-
2007
- 2007-04-12 US US11/734,350 patent/US20070185091A1/en not_active Abandoned
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2009
- 2009-11-24 US US12/624,875 patent/US20100069414A1/en not_active Abandoned
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2012
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