AU2001250570A1 - Dihydropyrimidine derivatives as cysteine protease inhibitors - Google Patents

Dihydropyrimidine derivatives as cysteine protease inhibitors

Info

Publication number: AU2001250570A1
Authority: AU; Australia
Prior art keywords: amino; alkyl; phenyl; methyl; compound according
Prior art date: 2000-10-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

AU2001250570A

Other languages

English (en)

Inventor

Qizhu Ding

Jadwiga Kaleta

Ronald G. Micetich

Andhe V. N. Reddy

Rajeshwar Singh

George Thomas

Nian E Zhou

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Naeja Pharmaceutical Inc

Original Assignee

Naeja Pharmaceutical Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-10-19

Filing date

2001-04-30

Publication date

2002-04-29

2001-04-30 Application filed by Naeja Pharmaceutical Inc filed Critical Naeja Pharmaceutical Inc

2002-04-29 Publication of AU2001250570A1 publication Critical patent/AU2001250570A1/en

Status Abandoned legal-status Critical Current

Links

WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical class C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 title claims description 9
239000002852 cysteine proteinase inhibitor Substances 0.000 title description 5
-1 benzyloxy, methylenedioxy, ethylenedioxy Chemical group 0.000 claims description 96
150000001875 compounds Chemical class 0.000 claims description 65
238000000034 method Methods 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 24
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
102000005927 Cysteine Proteases Human genes 0.000 claims description 15
108010005843 Cysteine Proteases Proteins 0.000 claims description 15
102000005600 Cathepsins Human genes 0.000 claims description 14
108010084457 Cathepsins Proteins 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 14
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 description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
230000000694 effects Effects 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
239000004305 biphenyl Substances 0.000 claims description 8
235000010290 biphenyl Nutrition 0.000 claims description 8
125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 7
239000012453 solvate Substances 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
208000001132 Osteoporosis Diseases 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
230000001404 mediated effect Effects 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
230000000172 allergic effect Effects 0.000 claims description 4
208000010668 atopic eczema Diseases 0.000 claims description 4
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001207 fluorophenyl group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
230000028993 immune response Effects 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
208000031225 myocardial ischemia Diseases 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
230000001537 neural effect Effects 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
208000035143 Bacterial infection Diseases 0.000 claims description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
206010027476 Metastases Diseases 0.000 claims description 3
206010028980 Neoplasm Diseases 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
239000001530 fumaric acid Substances 0.000 claims description 3
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
230000009401 metastasis Effects 0.000 claims description 3
229940098779 methanesulfonic acid Drugs 0.000 claims description 3
201000006938 muscular dystrophy Diseases 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
239000011975 tartaric acid Substances 0.000 claims description 3
235000002906 tartaric acid Nutrition 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 2
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 claims description 2
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
125000002723 alicyclic group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
159000000007 calcium salts Chemical class 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000005046 dihydronaphthyl group Chemical group 0.000 claims description 2
125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
150000002430 hydrocarbons Chemical group 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 claims description 2
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
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125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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125000001424 substituent group Chemical group 0.000 claims description 2
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
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125000000335 thiazolyl group Chemical group 0.000 claims description 2
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
229920002554 vinyl polymer Polymers 0.000 claims description 2
125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 44
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 32
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
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238000005160 1H NMR spectroscopy Methods 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 10
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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239000000843 powder Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
239000000047 product Substances 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
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159000000000 sodium salts Chemical class 0.000 description 1
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239000007787 solid Substances 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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235000000346 sugar Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000002278 tabletting lubricant Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
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239000000196 tragacanth Substances 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- C07D405/02—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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Immunology (AREA)
Oncology (AREA)
Neurology (AREA)
Vascular Medicine (AREA)
Pulmonology (AREA)
Tropical Medicine & Parasitology (AREA)
Biomedical Technology (AREA)
Communicable Diseases (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

AU2001250570A 2000-10-19 2001-04-30 Dihydropyrimidine derivatives as cysteine protease inhibitors Abandoned AU2001250570A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US24136000P	2000-10-19	2000-10-19
US60241360		2000-10-19
PCT/IB2001/000707 WO2002032879A1 (fr)	2000-10-19	2001-04-30	Derives de dihydropyrimidine utilises comme inhibiteurs de cysteine protease

Publications (1)

Publication Number	Publication Date
AU2001250570A1 true AU2001250570A1 (en)	2002-04-29

Family

ID=22910409

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001250570A Abandoned AU2001250570A1 (en)	2000-10-19	2001-04-30	Dihydropyrimidine derivatives as cysteine protease inhibitors

Country Status (6)

Country	Link
US (1)	US20040024000A1 (fr)
EP (1)	EP1326848A1 (fr)
JP (1)	JP2004511549A (fr)
AU (1)	AU2001250570A1 (fr)
CA (1)	CA2426271A1 (fr)
WO (1)	WO2002032879A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE0201980D0 (sv)	2002-06-24	2002-06-24	Astrazeneca Ab	Novel compounds
SE0201976D0 (sv) *	2002-06-24	2002-06-24	Astrazeneca Ab	Novel compounds
EP2251007A3 (fr)	2002-09-24	2011-03-23	Novartis AG	Agonistes du récepteur de la sphingosine-1-phosphate (S1P) pour son utilisation dans le traitement des maladies démyélinisantes
US8012950B2 (en) *	2003-08-29	2011-09-06	Wisconsin Alumni Research Foundation	Method to diagnose and treat degenerative joint disease
WO2009087379A2 (fr)	2008-01-09	2009-07-16	Amura Therapeutics Limited	Composés
KR20170081755A (ko)	2008-06-20	2017-07-12	노파르티스 아게	다발성 경화증을 치료하기 위한 소아용 조성물
PE20140471A1 (es)	2011-01-04	2014-04-13	Novartis Ag	Moduladores de la via del complemento y usos de los mismos
US9388199B2 (en)	2012-06-28	2016-07-12	Novartis Ag	Pyrrolidine derivatives and their use as complement pathway modulators
ES2647124T3 (es)	2012-06-28	2017-12-19	Novartis Ag	Derivados de pirrolidina y su uso como moduladores de la ruta del complemento
ES2710491T3 (es)	2012-06-28	2019-04-25	Novartis Ag	Moduladores de la vía del complemento y sus usos
CN104640855B (zh)	2012-06-28	2017-08-29	诺华股份有限公司	补体途经调节剂及其用途
WO2014002052A1 (fr)	2012-06-28	2014-01-03	Novartis Ag	Dérivés pyrrolidine et leur utilisation en tant que modulateurs de la voie du complément
AU2013288319A1 (en)	2012-07-12	2015-02-05	Novartis Ag	Complement pathway modulators and uses thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3853845A (en) *	1971-08-18	1974-12-10	Icn Pharmaceuticals	5-n-aminoacyl-5-aminouridines
US5916887A (en) *	1996-09-23	1999-06-29	National Research Council Of Canada	4-substituted-3-(2-amino-2-cycloalkyl methyl)-acetamido azetidin-2-one derivatives as cysteine proteinase regulators
AR013079A1 (es) *	1997-05-06	2000-12-13	Smithkline Beecham Corp	Derivados sustituidos de tetrahidrofurano-3-onas, de tetrahidropirano-3- onas y tetrahidrotiofen-3-onas, un procedimiento para su preparacion unacomposicion farmaceutica de un medicamento util como inhibidores de proteasas e intermediarios
GB9907683D0 (en) *	1999-04-06	1999-05-26	Synphar Lab Inc	Substituted azetidin-2-ones as cysteine protease inhibitors
GB9917909D0 (en) *	1999-07-31	1999-09-29	Synphar Lab Inc	Cysteine protease inhibitors
JP2001139534A (ja) *	1999-11-16	2001-05-22	Yoshimitsu Nagao	バリン誘導体およびその用途

2001
- 2001-04-30 WO PCT/IB2001/000707 patent/WO2002032879A1/fr not_active Ceased
- 2001-04-30 AU AU2001250570A patent/AU2001250570A1/en not_active Abandoned
- 2001-04-30 EP EP01923889A patent/EP1326848A1/fr not_active Withdrawn
- 2001-04-30 US US10/398,938 patent/US20040024000A1/en not_active Abandoned
- 2001-04-30 JP JP2002536262A patent/JP2004511549A/ja active Pending
- 2001-04-30 CA CA002426271A patent/CA2426271A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
JP2004511549A (ja)	2004-04-15
EP1326848A1 (fr)	2003-07-16
CA2426271A1 (fr)	2002-04-25
WO2002032879A1 (fr)	2002-04-25
US20040024000A1 (en)	2004-02-05

Publication	Publication Date	Title
JP2768554B2 (ja)	1998-06-25	金属タンパク質加水分解酵素阻害剤であるヒドロキサム酸誘導体
US6635621B1 (en)	2003-10-21	Cysteine protease inhibitors
US5714484A (en)	1998-02-03	α-(1,3-dicarbonylenol ether) methyl ketones as cysteine protease inhibitors
US6380220B1 (en)	2002-04-30	Derivatives from piperidine-keto acid, their preparation and use
AU2001250570A1 (en)	2002-04-29	Dihydropyrimidine derivatives as cysteine protease inhibitors
KR20000035402A (ko)	2000-06-26	시클릭 아미드 유도체
US6569847B1 (en)	2003-05-27	Substituted azetidin-2-ones as cysteine protease inhibitors
AU7365198A (en)	1998-11-24	Protease inhibitors
JP2001513767A (ja)	2001-09-04	メタロプロテアーゼ阻害剤としての逆ヒドロキサメート誘導体
JP2011511089A (ja)	2011-04-07	カテプシンｂの阻害剤
WO1997003060A1 (fr)	1997-01-30	Derives de la piperazine et leurs utilisations
JP2628820B2 (ja)	1997-07-09	アミノ酸誘導体及びその医薬品としての利用
JP3410476B2 (ja)	2003-05-26	新規なエポキシコハク酸アミド誘導体又はその塩
JP3892187B2 (ja)	2007-03-14	環状アミド誘導体
US20020049316A1 (en)	2002-04-25	Protease inhibitors
JPH06102639B2 (ja)	1994-12-14	アミノ酸誘導体
WO2007052938A1 (fr)	2007-05-10	Dérivés d’alkylcarbamoylnaphtalényloxyocténoylhydroxyamide présentant une activité inhibitrice vis-à-vis de l'histone désacétylase et synthèse desdits dérivés
WO1999048911A1 (fr)	1999-09-30	Monobactams inhibiteurs d'enzymes
JP2526084B2 (ja)	1996-08-21	新規なチアゾリジン誘導体
JP2006076989A (ja)	2006-03-23	α−ケトアミド誘導体、その製造方法、及びその用途
US6852882B2 (en)	2005-02-08	Peptide deformylase inhibitors
JP4312672B2 (ja)	2009-08-12	新規カルボン酸誘導体
JP4312656B2 (ja)	2009-08-12	新規なヒドロキシカルボン酸誘導体
JP4265993B2 (ja)	2009-05-20	新規なカルボン酸誘導体
JP4312657B2 (ja)	2009-08-12	新規なヒドロキシカルボキサミド誘導体

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Date	Code	Title	Description
2007-01-04	MK4	Application lapsed section 142(2)(d) - no continuation fee paid for the application