UA101021C2 - Конденсированная гетероциклическая производная и ее применение - Google Patents
Конденсированная гетероциклическая производная и ее применение Download PDFInfo
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- UA101021C2 UA101021C2 UAA201011405A UAA201011405A UA101021C2 UA 101021 C2 UA101021 C2 UA 101021C2 UA A201011405 A UAA201011405 A UA A201011405A UA A201011405 A UAA201011405 A UA A201011405A UA 101021 C2 UA101021 C2 UA 101021C2
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- Ukraine
- Prior art keywords
- optionally
- compound
- substituent
- oxo
- alkyl
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- 125000000623 heterocyclic group Chemical group 0.000 title description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 425
- 125000001424 substituent group Chemical group 0.000 claims abstract description 282
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 136
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 29
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims description 133
- 238000000034 method Methods 0.000 claims description 122
- 239000003795 chemical substances by application Substances 0.000 claims description 54
- 239000003112 inhibitor Substances 0.000 claims description 48
- 206010028980 Neoplasm Diseases 0.000 claims description 44
- 201000011510 cancer Diseases 0.000 claims description 37
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000008177 pharmaceutical agent Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 12
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 7
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 229940127557 pharmaceutical product Drugs 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- -1 methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino Chemical group 0.000 description 343
- 239000000243 solution Substances 0.000 description 148
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 103
- 239000000203 mixture Substances 0.000 description 90
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- 239000002552 dosage form Substances 0.000 description 74
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 74
- 238000006243 chemical reaction Methods 0.000 description 73
- 239000002904 solvent Substances 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 125000005843 halogen group Chemical group 0.000 description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 57
- 239000003814 drug Substances 0.000 description 56
- 235000002639 sodium chloride Nutrition 0.000 description 56
- 235000019441 ethanol Nutrition 0.000 description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 52
- 125000003545 alkoxy group Chemical group 0.000 description 51
- 125000003118 aryl group Chemical group 0.000 description 51
- 238000002360 preparation method Methods 0.000 description 51
- 229940079593 drug Drugs 0.000 description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- 238000005160 1H NMR spectroscopy Methods 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 150000002430 hydrocarbons Chemical group 0.000 description 36
- 229910052731 fluorine Inorganic materials 0.000 description 35
- 125000001153 fluoro group Chemical group F* 0.000 description 35
- 239000000546 pharmaceutical excipient Substances 0.000 description 34
- 239000000843 powder Substances 0.000 description 34
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 33
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- 125000003282 alkyl amino group Chemical group 0.000 description 30
- 239000011248 coating agent Substances 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 230000002411 adverse Effects 0.000 description 29
- 150000002170 ethers Chemical class 0.000 description 29
- 229940052303 ethers for general anesthesia Drugs 0.000 description 29
- 230000002829 reductive effect Effects 0.000 description 29
- 150000001408 amides Chemical class 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- 239000000126 substance Substances 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 26
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- 238000002347 injection Methods 0.000 description 22
- 229940126601 medicinal product Drugs 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 21
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- 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 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 19
- 125000004093 cyano group Chemical group *C#N 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 150000001298 alcohols Chemical class 0.000 description 18
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 18
- ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 description 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 17
- 108090000623 proteins and genes Proteins 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
- 238000013268 sustained release Methods 0.000 description 16
- 239000012730 sustained-release form Substances 0.000 description 16
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 15
- 239000000314 lubricant Substances 0.000 description 15
- 230000035484 reaction time Effects 0.000 description 15
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
- 239000002202 Polyethylene glycol Substances 0.000 description 13
- 229920002472 Starch Polymers 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 13
- 229920001223 polyethylene glycol Polymers 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 13
- 239000003381 stabilizer Substances 0.000 description 13
- 239000008107 starch Substances 0.000 description 13
- 235000019698 starch Nutrition 0.000 description 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- 150000002825 nitriles Chemical class 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
- 239000001768 carboxy methyl cellulose Substances 0.000 description 11
- 230000010261 cell growth Effects 0.000 description 11
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- 229910052801 chlorine Inorganic materials 0.000 description 11
- 235000015165 citric acid Nutrition 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- LOAUVZALPPNFOQ-UHFFFAOYSA-M quinaldate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-M 0.000 description 11
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
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- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
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- 125000004104 aryloxy group Chemical group 0.000 description 9
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 9
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- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- 229960004982 vinblastine sulfate Drugs 0.000 description 1
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 1
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- 229960005212 vindesine sulfate Drugs 0.000 description 1
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- 229960002066 vinorelbine Drugs 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229950009268 zinostatin Drugs 0.000 description 1
- FYQZGCBXYVWXSP-STTFAQHVSA-N zinostatin stimalamer Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1OC1C/2=C/C#C[C@H]3O[C@@]3([C@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(C)C=CC2=C(C)C=C(OC)C=C12 FYQZGCBXYVWXSP-STTFAQHVSA-N 0.000 description 1
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- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Данное изобретение касается соединения, имеющего сильное Smo-ингибиторное воздействие и низкую токсичность, которое является в достаточной мере удовлетворительным в качестве фармацевтического продукта.Данное изобретение касается соединения, представленного формулой, (I)в которой кольцо А является 7-членным кольцом, которое необязательно имеет заместитель(и), причем заместители необязательно связаны друг с другом с образованием кольца; X означает О, S или NR(Rозначает атом водорода или углеводную группу, необязательно имеющую заместитель(и)); Rозначает карбамоил, необязательно имеющий заместитель(и); и Rозначает гидрокси, необязательно имеющий заместитель(и), или его соли.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008045134 | 2008-02-26 | ||
| PCT/JP2009/054007 WO2009107850A2 (en) | 2008-02-26 | 2009-02-25 | Fused heterocyclic derivative and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA101021C2 true UA101021C2 (ru) | 2013-02-25 |
Family
ID=51586279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA201011405A UA101021C2 (ru) | 2008-02-26 | 2009-02-25 | Конденсированная гетероциклическая производная и ее применение |
Country Status (1)
| Country | Link |
|---|---|
| UA (1) | UA101021C2 (ru) |
-
2009
- 2009-02-25 UA UAA201011405A patent/UA101021C2/ru unknown
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