DE10358814A1 - Prolinylarylacetamide - Google Patents
Prolinylarylacetamide Download PDFInfo
- Publication number
- DE10358814A1 DE10358814A1 DE10358814A DE10358814A DE10358814A1 DE 10358814 A1 DE10358814 A1 DE 10358814A1 DE 10358814 A DE10358814 A DE 10358814A DE 10358814 A DE10358814 A DE 10358814A DE 10358814 A1 DE10358814 A1 DE 10358814A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- amide
- methyl
- amino
- hydroxy
- Prior art date
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 130
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 108010074860 Factor Xa Proteins 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 239000003112 inhibitor Substances 0.000 claims abstract description 6
- -1 COOA Chemical group 0.000 claims description 145
- 150000003839 salts Chemical class 0.000 claims description 69
- HHDQVBSXYDRQGD-QWWZWVQMSA-N (2r,4r)-4-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound O[C@@H]1C[C@H](C(O)=O)N(C(O)=O)C1 HHDQVBSXYDRQGD-QWWZWVQMSA-N 0.000 claims description 61
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 56
- 239000012453 solvate Substances 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 208000007536 Thrombosis Diseases 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 108010054265 Factor VIIa Proteins 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 208000006011 Stroke Diseases 0.000 claims description 7
- 238000002399 angioplasty Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000010125 myocardial infarction Diseases 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 206010022562 Intermittent claudication Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 208000037803 restenosis Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- QEIHSYGISQYKFL-UHFFFAOYSA-N n-(4-aminophenyl)-2-chloro-n-methylacetamide Chemical compound ClCC(=O)N(C)C1=CC=C(N)C=C1 QEIHSYGISQYKFL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 208000024980 claudication Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- FXTJCYDXMWCGAE-UHFFFAOYSA-N n-(4-aminophenyl)-2-(dimethylamino)-n-methylacetamide Chemical compound CN(C)CC(=O)N(C)C1=CC=C(N)C=C1 FXTJCYDXMWCGAE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- HIVWIEDJMNQQRT-UHFFFAOYSA-N n-(4-aminophenyl)-2-methoxy-n-methylacetamide Chemical compound COCC(=O)N(C)C1=CC=C(N)C=C1 HIVWIEDJMNQQRT-UHFFFAOYSA-N 0.000 claims description 3
- XJDZERKGXWDYKG-UHFFFAOYSA-N CCNCC(N(C)C(C=C1)=CC=C1N)=O Chemical compound CCNCC(N(C)C(C=C1)=CC=C1N)=O XJDZERKGXWDYKG-UHFFFAOYSA-N 0.000 claims description 2
- IXMHVXXUOFWZLK-UHFFFAOYSA-N N-(4-amino-3-fluorophenyl)-2-(dimethylamino)-N-methylacetamide Chemical compound CN(C)CC(=O)N(C)C1=CC(=C(C=C1)N)F IXMHVXXUOFWZLK-UHFFFAOYSA-N 0.000 claims description 2
- YXUPMMCDWICWRV-UHFFFAOYSA-N N-(4-amino-3-fluorophenyl)-2-methoxy-N-methylacetamide Chemical compound COCC(=O)N(C)C1=CC=C(N)C(F)=C1 YXUPMMCDWICWRV-UHFFFAOYSA-N 0.000 claims description 2
- NHEWNMVZHMFTPU-UHFFFAOYSA-N N-(4-aminophenyl)-2-(2,6-dimethylmorpholin-4-yl)-N-methylacetamide Chemical compound C1C(C)OC(C)CN1CC(=O)N(C)C1=CC=C(N)C=C1 NHEWNMVZHMFTPU-UHFFFAOYSA-N 0.000 claims description 2
- HGZIVFJSHCCKJL-UHFFFAOYSA-N N-(4-aminophenyl)-2-(4-hydroxypiperidin-1-yl)-N-methylacetamide Chemical compound C=1C=C(N)C=CC=1N(C)C(=O)CN1CCC(O)CC1 HGZIVFJSHCCKJL-UHFFFAOYSA-N 0.000 claims description 2
- QKFJNGKSEAXNQP-UHFFFAOYSA-N N-(4-aminophenyl)-2-(cyclohexylamino)-N-methylacetamide Chemical compound CN(C1=CC=C(C=C1)N)C(=O)CNC2CCCCC2 QKFJNGKSEAXNQP-UHFFFAOYSA-N 0.000 claims description 2
- GEDKUVJVXNOQHG-UHFFFAOYSA-N N-(4-aminophenyl)-2-(cyclopropylmethylamino)-N-methylacetamide Chemical compound CN(C1=CC=C(C=C1)N)C(=O)CNCC2CC2 GEDKUVJVXNOQHG-UHFFFAOYSA-N 0.000 claims description 2
- ACVCMUZHOXTZGO-UHFFFAOYSA-N N-(4-aminophenyl)-2-[3-(cyclohexylmethyl)piperidin-1-yl]-N-methylacetamide Chemical compound CN(C1=CC=C(C=C1)N)C(=O)CN2CCCC(C2)CC3CCCCC3 ACVCMUZHOXTZGO-UHFFFAOYSA-N 0.000 claims description 2
- ZWAPCTUERXVNDE-UHFFFAOYSA-N N-(4-aminophenyl)-N-methyl-2-(2-methylimidazol-1-yl)acetamide Chemical compound C=1C=C(N)C=CC=1N(C)C(=O)CN1C=CN=C1C ZWAPCTUERXVNDE-UHFFFAOYSA-N 0.000 claims description 2
- KMKIXWMTCOVOOD-UHFFFAOYSA-N N-(4-aminophenyl)-N-methyl-2-(methylamino)acetamide Chemical compound CNCC(=O)N(C)C1=CC=C(C=C1)N KMKIXWMTCOVOOD-UHFFFAOYSA-N 0.000 claims description 2
- VBRAHAVGFJYINX-UHFFFAOYSA-N N-(4-aminophenyl)-N-methyl-2-(propan-2-ylamino)acetamide Chemical compound CC(C)NCC(=O)N(C)C1=CC=C(C=C1)N VBRAHAVGFJYINX-UHFFFAOYSA-N 0.000 claims description 2
- MATIVMNAYVKWJE-UHFFFAOYSA-N N-(4-aminophenyl)-N-methyl-2-propoxyacetamide Chemical compound CCCOCC(=O)N(C)C1=CC=C(N)C=C1 MATIVMNAYVKWJE-UHFFFAOYSA-N 0.000 claims description 2
- QUGWUQDXDFDIIM-UHFFFAOYSA-N N-(6-aminopyridin-3-yl)-2-(dimethylamino)-N-methylacetamide Chemical compound CN(C)CC(=O)N(C)C1=CN=C(C=C1)N QUGWUQDXDFDIIM-UHFFFAOYSA-N 0.000 claims description 2
- KHCBNRYAAGMYRW-UHFFFAOYSA-N N-(6-aminopyridin-3-yl)-2-methoxy-N-methylacetamide Chemical compound CN(C1=CN=C(C=C1)N)C(=O)COC KHCBNRYAAGMYRW-UHFFFAOYSA-N 0.000 claims description 2
- MKIZQIPAEYHENT-UHFFFAOYSA-N [2-(4-amino-N-methylanilino)-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)N(C)C1=CC=C(C=C1)N MKIZQIPAEYHENT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 2
- PLWBMFWDDNDRRZ-YOQGVNIDSA-N methyl (2r)-2-[[2-[4-[[(4r)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-n-methylanilino]-2-oxoethyl]amino]-4-methylpentanoate Chemical compound C1=CC(N(C)C(=O)CN[C@H](CC(C)C)C(=O)OC)=CC=C1NC(=O)C1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 PLWBMFWDDNDRRZ-YOQGVNIDSA-N 0.000 claims description 2
- IRXSLDSGVBCBSS-UHFFFAOYSA-N n-(4-aminophenyl)-2-(diethylamino)-n-methylacetamide Chemical compound CCN(CC)CC(=O)N(C)C1=CC=C(N)C=C1 IRXSLDSGVBCBSS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- CYHGSZJHRCVXCB-UHFFFAOYSA-N N-(4-aminophenyl)-2-(tert-butylamino)-N-methylacetamide Chemical compound CC(C)(C)NCC(=O)N(C)C1=CC=C(C=C1)N CYHGSZJHRCVXCB-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 9
- 230000009424 thromboembolic effect Effects 0.000 abstract description 4
- 238000011321 prophylaxis Methods 0.000 abstract description 3
- 235000002639 sodium chloride Nutrition 0.000 description 44
- CCKMOMWZDSMYPX-NXEZZACHSA-N (2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carboxylic acid Chemical compound C1[C@H](O)C[C@H](C(O)=O)N1C(=O)NC1=CC=C(Cl)C=C1 CCKMOMWZDSMYPX-NXEZZACHSA-N 0.000 description 33
- 239000004480 active ingredient Substances 0.000 description 23
- 239000002585 base Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 239000008194 pharmaceutical composition Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
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- 239000003826 tablet Substances 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 108090000190 Thrombin Proteins 0.000 description 9
- 229960004072 thrombin Drugs 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
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- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 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 description 6
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- 239000011575 calcium Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 108010048049 Factor IXa Proteins 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 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 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
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- 229920006324 polyoxymethylene Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
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- 239000011241 protective layer Substances 0.000 description 1
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- 150000003212 purines Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003354 serine derivatives Chemical class 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10358814A DE10358814A1 (de) | 2003-12-16 | 2003-12-16 | Prolinylarylacetamide |
| JP2006544256A JP4800969B2 (ja) | 2003-12-16 | 2004-11-26 | プロリニルアリールアセトアミド |
| CNA2004800376989A CN1894210A (zh) | 2003-12-16 | 2004-11-26 | 脯氨酸基芳基乙酰胺 |
| MXPA06006740A MXPA06006740A (es) | 2003-12-16 | 2004-11-26 | Prolinilarilacetamidas. |
| ES04820404T ES2310772T3 (es) | 2003-12-16 | 2004-11-26 | Prolinilarilacetamidas. |
| RU2006125509/04A RU2006125509A (ru) | 2003-12-16 | 2004-11-26 | Полиниларилацетамиды |
| BRPI0417630-8A BRPI0417630A (pt) | 2003-12-16 | 2004-11-26 | prolinilarilacetamidas |
| DE502004007959T DE502004007959D1 (de) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamide |
| KR1020067011704A KR20060113729A (ko) | 2003-12-16 | 2004-11-26 | 프롤리닐아릴아세트아미드 |
| PCT/EP2004/013509 WO2005058817A1 (de) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamide |
| US10/583,094 US7732481B2 (en) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamides |
| EP04820404A EP1697318B1 (de) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamide |
| AT04820404T ATE406350T1 (de) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamide |
| AU2004299197A AU2004299197B2 (en) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamides |
| CA002549589A CA2549589A1 (en) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamides |
| ARP040104656A AR046765A1 (es) | 2003-12-16 | 2004-12-15 | Prolinilarilacetamidas |
| ZA200605841A ZA200605841B (en) | 2003-12-16 | 2006-07-14 | Prolinylarylacetamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10358814A DE10358814A1 (de) | 2003-12-16 | 2003-12-16 | Prolinylarylacetamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10358814A1 true DE10358814A1 (de) | 2005-07-21 |
Family
ID=34683363
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10358814A Withdrawn DE10358814A1 (de) | 2003-12-16 | 2003-12-16 | Prolinylarylacetamide |
| DE502004007959T Expired - Lifetime DE502004007959D1 (de) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502004007959T Expired - Lifetime DE502004007959D1 (de) | 2003-12-16 | 2004-11-26 | Prolinylarylacetamide |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7732481B2 (https=) |
| EP (1) | EP1697318B1 (https=) |
| JP (1) | JP4800969B2 (https=) |
| KR (1) | KR20060113729A (https=) |
| CN (1) | CN1894210A (https=) |
| AR (1) | AR046765A1 (https=) |
| AT (1) | ATE406350T1 (https=) |
| AU (1) | AU2004299197B2 (https=) |
| BR (1) | BRPI0417630A (https=) |
| CA (1) | CA2549589A1 (https=) |
| DE (2) | DE10358814A1 (https=) |
| ES (1) | ES2310772T3 (https=) |
| MX (1) | MXPA06006740A (https=) |
| RU (1) | RU2006125509A (https=) |
| WO (1) | WO2005058817A1 (https=) |
| ZA (1) | ZA200605841B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1818330A1 (de) | 2006-02-14 | 2007-08-15 | Boehringer Ingelheim Pharma GmbH & Co.KG | Substituierte Prolinamide, deren Herstellung und deren Verwendung als Arzneimittel |
| MY146623A (en) | 2006-05-16 | 2012-09-14 | Boehringer Ingelheim Int | Substituted prolinamides, manufacturing, and the use thereof as medicaments |
| WO2009000878A1 (en) * | 2007-06-28 | 2008-12-31 | Novartis Ag | Kallikrein 7 modulators |
| WO2011027888A1 (ja) * | 2009-09-07 | 2011-03-10 | 大日本住友製薬株式会社 | ジアミド－フェニル誘導体、またはその薬学的に許容される塩 |
| CN109761957B (zh) * | 2019-01-18 | 2020-05-19 | 西安交通大学 | 一种含有羟脯氨酸的化合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7030141B2 (en) | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| BRPI0408444A (pt) * | 2003-04-03 | 2006-04-04 | Merck Patent Gmbh | derivados de 1-n-(fenil)-2-n-(fenil) pirazolidina-1,2-dicarboxamida como inibidores de fator xa de coagulação para o tratamento de trombose |
| PL377633A1 (pl) * | 2003-04-03 | 2006-02-06 | Merck Patent Gmbh | Związki karbonylowe |
| DE102004014945A1 (de) * | 2004-03-26 | 2005-10-13 | Merck Patent Gmbh | Prolinylderivate |
-
2003
- 2003-12-16 DE DE10358814A patent/DE10358814A1/de not_active Withdrawn
-
2004
- 2004-11-26 AU AU2004299197A patent/AU2004299197B2/en not_active Ceased
- 2004-11-26 RU RU2006125509/04A patent/RU2006125509A/ru not_active Application Discontinuation
- 2004-11-26 US US10/583,094 patent/US7732481B2/en not_active Expired - Fee Related
- 2004-11-26 AT AT04820404T patent/ATE406350T1/de not_active IP Right Cessation
- 2004-11-26 JP JP2006544256A patent/JP4800969B2/ja not_active Expired - Fee Related
- 2004-11-26 MX MXPA06006740A patent/MXPA06006740A/es not_active Application Discontinuation
- 2004-11-26 KR KR1020067011704A patent/KR20060113729A/ko not_active Withdrawn
- 2004-11-26 WO PCT/EP2004/013509 patent/WO2005058817A1/de not_active Ceased
- 2004-11-26 CN CNA2004800376989A patent/CN1894210A/zh active Pending
- 2004-11-26 CA CA002549589A patent/CA2549589A1/en not_active Abandoned
- 2004-11-26 BR BRPI0417630-8A patent/BRPI0417630A/pt not_active Application Discontinuation
- 2004-11-26 ES ES04820404T patent/ES2310772T3/es not_active Expired - Lifetime
- 2004-11-26 DE DE502004007959T patent/DE502004007959D1/de not_active Expired - Lifetime
- 2004-11-26 EP EP04820404A patent/EP1697318B1/de not_active Expired - Lifetime
- 2004-12-15 AR ARP040104656A patent/AR046765A1/es unknown
-
2006
- 2006-07-14 ZA ZA200605841A patent/ZA200605841B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060113729A (ko) | 2006-11-02 |
| DE502004007959D1 (de) | 2008-10-09 |
| ZA200605841B (en) | 2007-10-31 |
| US7732481B2 (en) | 2010-06-08 |
| JP4800969B2 (ja) | 2011-10-26 |
| CN1894210A (zh) | 2007-01-10 |
| AU2004299197B2 (en) | 2010-08-05 |
| EP1697318B1 (de) | 2008-08-27 |
| MXPA06006740A (es) | 2006-08-18 |
| US20070185189A1 (en) | 2007-08-09 |
| WO2005058817A1 (de) | 2005-06-30 |
| ATE406350T1 (de) | 2008-09-15 |
| JP2007513988A (ja) | 2007-05-31 |
| EP1697318A1 (de) | 2006-09-06 |
| AR046765A1 (es) | 2005-12-21 |
| RU2006125509A (ru) | 2008-01-27 |
| CA2549589A1 (en) | 2005-06-30 |
| ES2310772T3 (es) | 2009-01-16 |
| BRPI0417630A (pt) | 2007-03-27 |
| AU2004299197A1 (en) | 2005-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |