NO301118B1 - Pyrroloimidazolyl- og imidazopyridinylsubstituerte 1H-benzimidazolderivater som aromatasehemmere - Google Patents
Pyrroloimidazolyl- og imidazopyridinylsubstituerte 1H-benzimidazolderivater som aromatasehemmere Download PDFInfo
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- NO301118B1 NO301118B1 NO942748A NO942748A NO301118B1 NO 301118 B1 NO301118 B1 NO 301118B1 NO 942748 A NO942748 A NO 942748A NO 942748 A NO942748 A NO 942748A NO 301118 B1 NO301118 B1 NO 301118B1
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- Prior art keywords
- acid
- formula
- phenyl
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- compounds
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- -1 Pyrroloimidazolyl Chemical group 0.000 title abstract description 34
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 title abstract 2
- 239000003886 aromatase inhibitor Substances 0.000 title description 3
- 229940046844 aromatase inhibitors Drugs 0.000 title description 3
- HYZJCKYKOHLVJF-SFIIULIVSA-N 1H-benzimidazole Chemical class C1=CC=C2N[11CH]=NC2=C1 HYZJCKYKOHLVJF-SFIIULIVSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003163 gonadal steroid hormone Substances 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 2
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 45
- 230000015572 biosynthetic process Effects 0.000 abstract description 12
- 241000124008 Mammalia Species 0.000 abstract description 6
- 150000002431 hydrogen Chemical class 0.000 abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
- 125000004193 piperazinyl group Chemical group 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 125000002757 morpholinyl group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
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- ZOEFCCMDUURGSE-SQKVDDBVSA-N cosyntropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 ZOEFCCMDUURGSE-SQKVDDBVSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 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
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- BGWMHFKCAUBYJJ-UHFFFAOYSA-N ethyl 2-chloroethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CCl BGWMHFKCAUBYJJ-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- JMIAPORGEDIDLT-UHFFFAOYSA-N ethyl ethanimidate Chemical compound CCOC(C)=N JMIAPORGEDIDLT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000002622 gonadotropin Substances 0.000 description 1
- 201000000079 gynecomastia Diseases 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 description 1
- 239000003906 humectant Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical class C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 208000008634 oligospermia Diseases 0.000 description 1
- 230000036616 oligospermia Effects 0.000 description 1
- 231100000528 oligospermia Toxicity 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001325 propanoyl 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82656492A | 1992-01-27 | 1992-01-27 | |
| PCT/EP1993/000129 WO1993015079A1 (en) | 1992-01-27 | 1993-01-20 | Pyrroloimidazolyl and imidazopyridinyl substituted 1h-benzimidazole derivatives as aromatase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO942748D0 NO942748D0 (no) | 1994-07-22 |
| NO942748L NO942748L (no) | 1994-09-26 |
| NO301118B1 true NO301118B1 (no) | 1997-09-15 |
Family
ID=25246906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO942748A NO301118B1 (no) | 1992-01-27 | 1994-07-22 | Pyrroloimidazolyl- og imidazopyridinylsubstituerte 1H-benzimidazolderivater som aromatasehemmere |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0625155B1 (zh) |
| JP (1) | JPH07503242A (zh) |
| KR (1) | KR100263412B1 (zh) |
| CN (2) | CN1036007C (zh) |
| AT (1) | ATE203992T1 (zh) |
| AU (1) | AU668708B2 (zh) |
| CA (1) | CA2127689A1 (zh) |
| DE (1) | DE69330557T2 (zh) |
| DK (1) | DK0625155T3 (zh) |
| ES (1) | ES2161714T3 (zh) |
| FI (1) | FI106462B (zh) |
| GR (1) | GR3036545T3 (zh) |
| HU (1) | HU222117B1 (zh) |
| IL (1) | IL104498A (zh) |
| MX (1) | MX9300412A (zh) |
| NO (1) | NO301118B1 (zh) |
| PT (1) | PT625155E (zh) |
| TW (1) | TW221690B (zh) |
| WO (1) | WO1993015079A1 (zh) |
| ZA (1) | ZA93561B (zh) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6015796A (en) * | 1995-06-14 | 1997-01-15 | Yamanouchi Pharmaceutical Co., Ltd. | Fused imidazole derivatives and medicinal composition thereof |
| NZ526387A (en) * | 2000-11-17 | 2004-02-27 | Takeda Chemical Industries Ltd | Imidazole derivatives having a steroid C17,20-lyase- inhibitory activity, their production process and use thereof |
| US20060148893A1 (en) * | 2003-06-10 | 2006-07-06 | Blanc Jean-Baptiste E | Chemical compounds |
| CN100496525C (zh) * | 2004-04-02 | 2009-06-10 | 李嫦梅 | 从洋蓟根、茎、叶中提取活性成份的方法及其应用 |
| CN1968930A (zh) * | 2004-05-28 | 2007-05-23 | 斯皮德尔实验股份公司 | 作为芳化酶抑制剂的双环含氮杂环 |
| JP2008500999A (ja) * | 2004-05-28 | 2008-01-17 | シュペーデル・エクスペリメンタ・アーゲー | 複素環式化合物およびアルドステロンシンターゼ阻害薬としてのそれらの使用 |
| BRPI0510410A (pt) * | 2004-05-28 | 2007-10-23 | Speedel Experimenta Ag | compostos orgánicos |
| WO2006005725A2 (en) * | 2004-07-09 | 2006-01-19 | Speedel Experimenta Ag | N containing condensed heterocycles with antitumor effects |
| WO2006093353A1 (ja) | 2005-03-03 | 2006-09-08 | Takeda Pharmaceutical Company Limited | 放出制御組成物 |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| CN101250559B (zh) * | 2008-03-14 | 2010-12-29 | 厦门大学 | 一种利用天然抗菌剂防治酒精发酵染菌的方法 |
| JO3137B1 (ar) | 2012-01-17 | 2017-09-20 | Novartis Ag | أملاح وأشكال جديدة لمثبط إنزيم سينثاز أو أروماتاز ثنائي هيدروبيرولو [2،1-c] إيميدازوليل ألدوستيرون |
| CN106665636A (zh) * | 2015-11-07 | 2017-05-17 | 郑州明德生物科技有限公司 | 采用月桂酰精氨酸乙酯抑制酒精发酵污染微生物的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4426450A (en) * | 1981-08-24 | 1984-01-17 | Fermentec Corporation | Fermentation process and apparatus |
| GB8820730D0 (en) * | 1988-09-02 | 1988-10-05 | Erba Carlo Spa | Substituted 5 6 7 8-tetrahydroimidazo/1.5-a/pyridines & process for their preparation |
| CA2026792A1 (en) * | 1989-11-01 | 1991-05-02 | Michael N. Greco | (6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1h-benzotriazole derivatives |
| US5059431A (en) * | 1990-12-07 | 1991-10-22 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University | Process for deacidifying wine |
-
1993
- 1993-01-20 KR KR1019940702246A patent/KR100263412B1/ko not_active IP Right Cessation
- 1993-01-20 DK DK93903211T patent/DK0625155T3/da active
- 1993-01-20 DE DE69330557T patent/DE69330557T2/de not_active Expired - Fee Related
- 1993-01-20 ES ES93903211T patent/ES2161714T3/es not_active Expired - Lifetime
- 1993-01-20 AU AU34505/93A patent/AU668708B2/en not_active Ceased
- 1993-01-20 JP JP5512909A patent/JPH07503242A/ja active Pending
- 1993-01-20 PT PT93903211T patent/PT625155E/pt unknown
- 1993-01-20 CA CA002127689A patent/CA2127689A1/en not_active Abandoned
- 1993-01-20 EP EP93903211A patent/EP0625155B1/en not_active Expired - Lifetime
- 1993-01-20 HU HU9402208A patent/HU222117B1/hu not_active IP Right Cessation
- 1993-01-20 AT AT93903211T patent/ATE203992T1/de not_active IP Right Cessation
- 1993-01-20 WO PCT/EP1993/000129 patent/WO1993015079A1/en active IP Right Grant
- 1993-01-21 TW TW082100454A patent/TW221690B/zh active
- 1993-01-25 IL IL10449893A patent/IL104498A/en not_active IP Right Cessation
- 1993-01-26 ZA ZA93561A patent/ZA93561B/xx unknown
- 1993-01-26 MX MX9300412A patent/MX9300412A/es unknown
- 1993-01-26 CN CN93100707A patent/CN1036007C/zh not_active Expired - Fee Related
- 1993-05-15 CN CN93107070A patent/CN1049687C/zh not_active Expired - Fee Related
-
1994
- 1994-07-22 NO NO942748A patent/NO301118B1/no not_active IP Right Cessation
- 1994-07-26 FI FI943511A patent/FI106462B/fi active
-
2001
- 2001-09-06 GR GR20010401398T patent/GR3036545T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR3036545T3 (en) | 2001-12-31 |
| JPH07503242A (ja) | 1995-04-06 |
| DK0625155T3 (da) | 2001-11-12 |
| AU668708B2 (en) | 1996-05-16 |
| NO942748L (no) | 1994-09-26 |
| CA2127689A1 (en) | 1993-08-05 |
| CN1049687C (zh) | 2000-02-23 |
| FI106462B (fi) | 2001-02-15 |
| WO1993015079A1 (en) | 1993-08-05 |
| DE69330557T2 (de) | 2002-06-20 |
| FI943511A0 (fi) | 1994-07-26 |
| FI943511A (fi) | 1994-07-26 |
| HU222117B1 (hu) | 2003-04-28 |
| HUT70853A (en) | 1995-11-28 |
| ATE203992T1 (de) | 2001-08-15 |
| AU3450593A (en) | 1993-09-01 |
| NO942748D0 (no) | 1994-07-22 |
| IL104498A (en) | 1996-07-23 |
| KR100263412B1 (ko) | 2000-08-01 |
| ES2161714T3 (es) | 2001-12-16 |
| HU9402208D0 (en) | 1994-09-28 |
| PT625155E (pt) | 2002-01-30 |
| EP0625155B1 (en) | 2001-08-08 |
| ZA93561B (en) | 1994-07-26 |
| CN1036007C (zh) | 1997-10-01 |
| MX9300412A (es) | 1993-07-01 |
| DE69330557D1 (de) | 2001-09-13 |
| CN1074907A (zh) | 1993-08-04 |
| IL104498A0 (en) | 1993-05-13 |
| EP0625155A1 (en) | 1994-11-23 |
| CN1095415A (zh) | 1994-11-23 |
| TW221690B (zh) | 1994-03-11 |
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