ZA200206298B - Heterocyclic side chain containing, N-substituted metalloprotease inhibitors. - Google Patents
Heterocyclic side chain containing, N-substituted metalloprotease inhibitors. Download PDFInfo
- Publication number
- ZA200206298B ZA200206298B ZA200206298A ZA200206298A ZA200206298B ZA 200206298 B ZA200206298 B ZA 200206298B ZA 200206298 A ZA200206298 A ZA 200206298A ZA 200206298 A ZA200206298 A ZA 200206298A ZA 200206298 B ZA200206298 B ZA 200206298B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- heterocycloalkyl
- heteroalkyl
- heteroaryl
- cycloalkyl
- Prior art date
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 5
- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 102000005741 Metalloproteases Human genes 0.000 claims description 20
- 108010006035 Metalloproteases Proteins 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 125000006413 ring segment Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
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- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 206010027476 Metastases Diseases 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 230000009401 metastasis Effects 0.000 claims description 2
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- 208000035475 disorder Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 244000237986 Melia azadirachta Species 0.000 claims 1
- 235000013500 Melia azadirachta Nutrition 0.000 claims 1
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- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- -1 spirocycle Chemical group 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
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- 125000002619 bicyclic group Chemical group 0.000 description 5
- 229940088598 enzyme Drugs 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229930194542 Keto Natural products 0.000 description 4
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
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- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000005323 thioketone group Chemical group 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N 3H-indole Chemical compound C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000029816 Collagenase Human genes 0.000 description 2
- 108060005980 Collagenase Proteins 0.000 description 2
- 108010026132 Gelatinases Proteins 0.000 description 2
- 102000013382 Gelatinases Human genes 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- 102000000422 Matrix Metalloproteinase 3 Human genes 0.000 description 2
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 2
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 101710204001 Zinc metalloprotease Proteins 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
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- 238000000034 method Methods 0.000 description 2
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- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
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- GCSSUGDABJOGTO-UHFFFAOYSA-N 1h-benzimidazole;1,3-benzothiazole;1,3-benzoxazole;9h-carbazole;pteridine Chemical compound C1=CC=C2NC=NC2=C1.C1=CC=C2OC=NC2=C1.C1=CC=C2SC=NC2=C1.N1=CN=CC2=NC=CN=C21.C1=CC=C2C3=CC=CC=C3NC2=C1 GCSSUGDABJOGTO-UHFFFAOYSA-N 0.000 description 1
- UFAQNAPJTMOSIX-UHFFFAOYSA-N 1h-indole;indolizine;pyrazine;pyridazine;pyridine;pyrimidine;1,3,5-triazine Chemical compound C1=CC=NC=C1.C1=CC=NN=C1.C1=CN=CN=C1.C1=CN=CC=N1.C1=NC=NC=N1.C1=CC=CN2C=CC=C21.C1=CC=C2NC=CC2=C1 UFAQNAPJTMOSIX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
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- YWOIQIYQBRDOQA-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-oxazine Chemical compound C1COC=NC1 YWOIQIYQBRDOQA-UHFFFAOYSA-N 0.000 description 1
- GMLMFZXBPRIXPK-UHFFFAOYSA-N 6h-1,3-oxazine Chemical compound C1OC=NC=C1 GMLMFZXBPRIXPK-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- REQRTGWACJQPDT-UHFFFAOYSA-N C1=CC=CC=2OC3=CC=CC=C3NC12.N=1CC=CC1 Chemical compound C1=CC=CC=2OC3=CC=CC=C3NC12.N=1CC=CC1 REQRTGWACJQPDT-UHFFFAOYSA-N 0.000 description 1
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- CKTDUXNQRASKKG-UHFFFAOYSA-N N1NCCCC1.S1CCSCC1.O1CCSCC1 Chemical compound N1NCCCC1.S1CCSCC1.O1CCSCC1 CKTDUXNQRASKKG-UHFFFAOYSA-N 0.000 description 1
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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- 101710172711 Structural protein Proteins 0.000 description 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- HPCJVWBXCCSQOK-UHFFFAOYSA-N acridine;phenazine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21.C1=CC=CC2=NC3=CC=CC=C3N=C21 HPCJVWBXCCSQOK-UHFFFAOYSA-N 0.000 description 1
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- 125000005336 allyloxy group Chemical group 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- OOZMOOPLAHIWOE-UHFFFAOYSA-N azetidine aziridine oxetane oxirane oxolane pyrrolidine Chemical compound N1CCCC1.O1CCCC1.N1CCC1.O1CCC1.N1CC1.O1CC1 OOZMOOPLAHIWOE-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
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- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
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- 235000001671 coumarin Nutrition 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- KAFRKUIBYDBECQ-UHFFFAOYSA-N dibenzofuran 1,2,4,5-tetrazine triazine 1,2,4-triazine Chemical compound C1=CC=CC=2OC3=C(C21)C=CC=C3.N3=NC=NN=C3.N3=NC=NC=C3.N3=NN=CC=C3 KAFRKUIBYDBECQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- LJCHSZRTMJEOKW-UHFFFAOYSA-N furan 1H-imidazole 1,2-oxazole 1,3-oxazole 1H-pyrazole 1H-pyrrole thiophene Chemical compound O1C=NC=C1.O1N=CC=C1.N1C=NC=C1.N1N=CC=C1.S1C=CC=C1.O1C=CC=C1.N1C=CC=C1 LJCHSZRTMJEOKW-UHFFFAOYSA-N 0.000 description 1
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- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
- OCSMOTCMPXTDND-OUAUKWLOSA-N marimastat Chemical compound CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO OCSMOTCMPXTDND-OUAUKWLOSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AHKJGIUKIBGOKH-UHFFFAOYSA-N morpholine;piperidine Chemical compound C1CCNCC1.C1COCCN1 AHKJGIUKIBGOKH-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
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- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
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- C—CHEMISTRY; METALLURGY
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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ZA200206298A ZA200206298B (en) | 2000-03-21 | 2002-08-07 | Heterocyclic side chain containing, N-substituted metalloprotease inhibitors. |
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US (2) | US6949545B2 (ja) |
EP (1) | EP1265864A1 (ja) |
JP (1) | JP2003528080A (ja) |
KR (1) | KR20020081465A (ja) |
CN (1) | CN1425004A (ja) |
AR (1) | AR030197A1 (ja) |
AU (1) | AU2001245891A1 (ja) |
BR (1) | BR0109328A (ja) |
CA (1) | CA2404131A1 (ja) |
CZ (1) | CZ20023145A3 (ja) |
HU (1) | HUP0300235A2 (ja) |
IL (1) | IL151125A0 (ja) |
MA (1) | MA26884A1 (ja) |
MX (1) | MXPA02009311A (ja) |
NO (1) | NO20024520L (ja) |
NZ (1) | NZ520657A (ja) |
PE (1) | PE20011137A1 (ja) |
PL (1) | PL365444A1 (ja) |
RU (1) | RU2245876C2 (ja) |
SK (1) | SK12842002A3 (ja) |
WO (1) | WO2001070691A1 (ja) |
ZA (1) | ZA200206298B (ja) |
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2001
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- 2001-03-02 JP JP2001568903A patent/JP2003528080A/ja not_active Withdrawn
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AR030197A1 (es) | 2003-08-13 |
NO20024520D0 (no) | 2002-09-20 |
JP2003528080A (ja) | 2003-09-24 |
US20030139414A1 (en) | 2003-07-24 |
PE20011137A1 (es) | 2001-12-04 |
MXPA02009311A (es) | 2003-03-12 |
HUP0300235A2 (hu) | 2003-08-28 |
NZ520657A (en) | 2004-11-26 |
WO2001070691A1 (en) | 2001-09-27 |
US20040127498A1 (en) | 2004-07-01 |
CN1425004A (zh) | 2003-06-18 |
MA26884A1 (fr) | 2004-12-20 |
CA2404131A1 (en) | 2001-09-27 |
CZ20023145A3 (cs) | 2003-01-15 |
AU2001245891A1 (en) | 2001-10-03 |
EP1265864A1 (en) | 2002-12-18 |
SK12842002A3 (sk) | 2003-02-04 |
US6949545B2 (en) | 2005-09-27 |
RU2245876C2 (ru) | 2005-02-10 |
BR0109328A (pt) | 2003-06-10 |
NO20024520L (no) | 2002-09-20 |
IL151125A0 (en) | 2003-04-10 |
PL365444A1 (en) | 2005-01-10 |
RU2002128007A (ru) | 2004-02-27 |
KR20020081465A (ko) | 2002-10-26 |
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