ZA200107185B - Bicyclic heterocycles, pharmaceutical compositions containing these compounds, and processes for preparing them. - Google Patents
Bicyclic heterocycles, pharmaceutical compositions containing these compounds, and processes for preparing them. Download PDFInfo
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- ZA200107185B ZA200107185B ZA200107185A ZA200107185A ZA200107185B ZA 200107185 B ZA200107185 B ZA 200107185B ZA 200107185 A ZA200107185 A ZA 200107185A ZA 200107185 A ZA200107185 A ZA 200107185A ZA 200107185 B ZA200107185 B ZA 200107185B
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- 150000001875 compounds Chemical class 0.000 title claims description 32
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- -1 methoxy, ethynyl Chemical group 0.000 claims description 119
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 31
- 125000003386 piperidinyl group Chemical group 0.000 claims description 26
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- FOUZISDNESEYLX-UHFFFAOYSA-N 2-(2-hydroxyethylazaniumyl)acetate Chemical class OCCNCC(O)=O FOUZISDNESEYLX-UHFFFAOYSA-N 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 210000000013 bile duct Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- SWPBXPQKXQIJCP-UHFFFAOYSA-N ethyl 2-[4-[3-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]oxy-2-hydroxypropyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC(O)COC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(Br)=C1 SWPBXPQKXQIJCP-UHFFFAOYSA-N 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000001149 thermolysis Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 33
- 125000003118 aryl group Chemical group 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005002 aryl methyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
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- 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
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- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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- 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
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- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| DE19911509A DE19911509A1 (de) | 1999-03-15 | 1999-03-15 | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
Publications (1)
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| ZA200107185B true ZA200107185B (en) | 2002-06-21 |
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Family Applications (1)
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| ZA200107185A ZA200107185B (en) | 1999-03-15 | 2001-08-30 | Bicyclic heterocycles, pharmaceutical compositions containing these compounds, and processes for preparing them. |
Country Status (35)
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| US (1) | US20020177601A1 (fr) |
| EP (1) | EP1163227B1 (fr) |
| JP (2) | JP3754617B2 (fr) |
| KR (1) | KR100749292B1 (fr) |
| CN (1) | CN1150171C (fr) |
| AR (1) | AR022939A1 (fr) |
| AT (1) | ATE305456T1 (fr) |
| AU (1) | AU772520B2 (fr) |
| BG (1) | BG65130B1 (fr) |
| BR (1) | BR0009076A (fr) |
| CA (1) | CA2368059C (fr) |
| CO (1) | CO5150216A1 (fr) |
| CZ (1) | CZ20013326A3 (fr) |
| DE (2) | DE19911509A1 (fr) |
| DK (1) | DK1163227T3 (fr) |
| EA (1) | EA005098B1 (fr) |
| EC (1) | ECSP034646A (fr) |
| EE (1) | EE05034B1 (fr) |
| ES (1) | ES2250111T3 (fr) |
| HK (1) | HK1043124B (fr) |
| HU (1) | HUP0201832A3 (fr) |
| IL (1) | IL144626A (fr) |
| ME (1) | MEP45608A (fr) |
| MY (1) | MY123642A (fr) |
| NO (1) | NO327747B1 (fr) |
| NZ (1) | NZ514706A (fr) |
| PL (1) | PL205726B1 (fr) |
| RS (1) | RS50062B (fr) |
| SK (1) | SK286959B6 (fr) |
| TR (1) | TR200102782T2 (fr) |
| TW (1) | TWI268924B (fr) |
| UA (1) | UA71610C2 (fr) |
| UY (1) | UY26066A1 (fr) |
| WO (1) | WO2000055141A1 (fr) |
| ZA (1) | ZA200107185B (fr) |
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| SK2142003A3 (en) | 2000-08-21 | 2003-07-01 | Astrazeneca Ab | Quinazoline derivatives, process for their preparation, pharmaceutical composition comprising same and their use |
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1999
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- 2000-03-14 WO PCT/EP2000/002228 patent/WO2000055141A1/fr active IP Right Grant
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- 2000-03-14 UA UA2001107007A patent/UA71610C2/uk unknown
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- 2000-03-14 KR KR1020017011645A patent/KR100749292B1/ko not_active IP Right Cessation
- 2000-03-15 AR ARP000101152A patent/AR022939A1/es not_active Suspension/Interruption
- 2000-03-15 MY MYPI20001028A patent/MY123642A/en unknown
- 2000-03-15 UY UY26066A patent/UY26066A1/es not_active IP Right Cessation
- 2000-04-26 TW TW089104508A patent/TWI268924B/zh not_active IP Right Cessation
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2001
- 2001-07-30 IL IL144626A patent/IL144626A/en not_active IP Right Cessation
- 2001-08-23 US US09/938,235 patent/US20020177601A1/en not_active Abandoned
- 2001-08-30 ZA ZA200107185A patent/ZA200107185B/en unknown
- 2001-09-12 BG BG105893A patent/BG65130B1/bg active Active
- 2001-09-14 NO NO20014487A patent/NO327747B1/no not_active IP Right Cessation
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2002
- 2002-06-25 HK HK02104697.6A patent/HK1043124B/zh not_active IP Right Cessation
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2003
- 2003-06-11 EC EC2003004646A patent/ECSP034646A/es unknown
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2005
- 2005-09-07 JP JP2005259571A patent/JP2006077010A/ja active Pending
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