LV13735B - Method for manufacturing substituted adamantylarylmagnesium chalogenides - Google Patents
Method for manufacturing substituted adamantylarylmagnesium chalogenides Download PDFInfo
- Publication number
- LV13735B LV13735B LV060151A LV060151A LV13735B LV 13735 B LV13735 B LV 13735B LV 060151 A LV060151 A LV 060151A LV 060151 A LV060151 A LV 060151A LV 13735 B LV13735 B LV 13735B
- Authority
- LV
- Latvia
- Prior art keywords
- reaction
- anhydrous
- group
- halides
- lithium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 74
- 150000004820 halides Chemical class 0.000 claims abstract description 56
- 239000011777 magnesium Substances 0.000 claims abstract description 30
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 27
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000003747 Grignard reaction Methods 0.000 claims abstract description 14
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract 6
- 159000000002 lithium salts Chemical class 0.000 claims abstract 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- -1 tetrafluoroborate Chemical compound 0.000 claims description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 8
- 229910052744 lithium Inorganic materials 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000012442 inert solvent Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 67
- 239000003153 chemical reaction reagent Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- QQAMHHZQONQBFZ-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)adamantane Chemical compound COC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 QQAMHHZQONQBFZ-UHFFFAOYSA-N 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- STGNTTPGWSZTMO-UHFFFAOYSA-N 1-(5-bromo-2,3-dimethoxyphenyl)adamantane Chemical compound COC1=CC(Br)=CC(C23CC4CC(CC(C4)C2)C3)=C1OC STGNTTPGWSZTMO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000004792 aryl magnesium halides Chemical class 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HYSZKSPAPGPYFQ-UHFFFAOYSA-N 1-(2-methoxyphenyl)adamantane Chemical compound COC1=CC=CC=C1C1(C2)CC(C3)CC2CC3C1 HYSZKSPAPGPYFQ-UHFFFAOYSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229960002916 adapalene Drugs 0.000 description 3
- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001502 aryl halides Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002901 organomagnesium compounds Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- FRPWQGROGLXUPZ-UHFFFAOYSA-N 1-(4-bromo-2-methoxyphenyl)adamantane Chemical compound COC1=CC(Br)=CC=C1C1(C2)CC(C3)CC2CC3C1 FRPWQGROGLXUPZ-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- LDGIHZJOIQSHPB-UHFFFAOYSA-N CD437 Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3C=C2)C(=O)O)=CC=C1O LDGIHZJOIQSHPB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- HOXDQGKKENOCRK-UHFFFAOYSA-M [Br-].C1C(C2)CC(C3)CC2CC13C1=CC([Mg+])=CC=C1OCC1=CC=CC=C1 Chemical compound [Br-].C1C(C2)CC(C3)CC2CC13C1=CC([Mg+])=CC=C1OCC1=CC=CC=C1 HOXDQGKKENOCRK-UHFFFAOYSA-M 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 150000001499 aryl bromides Chemical class 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 150000002681 magnesium compounds Chemical class 0.000 description 2
- 125000002734 organomagnesium group Chemical group 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- TWAKUARPZZSRLJ-UHFFFAOYSA-N 1-(2-bromophenyl)adamantane Chemical compound BrC1=CC=CC=C1C1(C2)CC(C3)CC2CC3C1 TWAKUARPZZSRLJ-UHFFFAOYSA-N 0.000 description 1
- INULLDUIYAKZOH-UHFFFAOYSA-N 1-(4-bromo-2-phenylmethoxyphenyl)adamantane Chemical compound C=1C(Br)=CC=C(C23CC4CC(CC(C4)C2)C3)C=1OCC1=CC=CC=C1 INULLDUIYAKZOH-UHFFFAOYSA-N 0.000 description 1
- GVLSPHCBVZUIKP-UHFFFAOYSA-N 1-(5-bromo-2-phenylmethoxyphenyl)adamantane Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(Br)=CC=C1OCC1=CC=CC=C1 GVLSPHCBVZUIKP-UHFFFAOYSA-N 0.000 description 1
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 1
- NBHAHMHUMMWFPJ-UHFFFAOYSA-N 1-bromo-2-phenylmethoxybenzene Chemical compound BrC1=CC=CC=C1OCC1=CC=CC=C1 NBHAHMHUMMWFPJ-UHFFFAOYSA-N 0.000 description 1
- GJLGGECBUUNDNQ-UHFFFAOYSA-N 2-(4-phenylphenyl)prop-2-enoic acid Chemical class C1=CC(C(=C)C(=O)O)=CC=C1C1=CC=CC=C1 GJLGGECBUUNDNQ-UHFFFAOYSA-N 0.000 description 1
- IWZNLKUVIIFUOG-UHFFFAOYSA-N 2-chloro-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(Cl)=CC1=CC=CC=C1 IWZNLKUVIIFUOG-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- HHDOELPGMRBQJZ-UHFFFAOYSA-N [2-(1-adamantyl)-5-bromophenoxy]-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC(Br)=CC=C1C1(C2)CC(C3)CC2CC3C1 HHDOELPGMRBQJZ-UHFFFAOYSA-N 0.000 description 1
- AOZRFSQSDGELGK-UHFFFAOYSA-N [3-(1-adamantyl)-4-methoxyphenyl]-phenylmethanol Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(OC)=CC=C1C(O)C1=CC=CC=C1 AOZRFSQSDGELGK-UHFFFAOYSA-N 0.000 description 1
- FPZOBRFHRPQGAA-UHFFFAOYSA-N [3-(1-adamantyl)-4-methoxyphenyl]boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1C1(C2)CC(C3)CC2CC3C1 FPZOBRFHRPQGAA-UHFFFAOYSA-N 0.000 description 1
- AIYARUNZTVUMQC-UHFFFAOYSA-M [Br-].CC(C)(C)[Si](C)(C)OC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 Chemical group [Br-].CC(C)(C)[Si](C)(C)OC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 AIYARUNZTVUMQC-UHFFFAOYSA-M 0.000 description 1
- CMFAVTSZPVDNME-UHFFFAOYSA-M [Br-].COC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 Chemical compound [Br-].COC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 CMFAVTSZPVDNME-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 230000006882 induction of apoptosis Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HZZOEADXZLYIHG-UHFFFAOYSA-N magnesiomagnesium Chemical compound [Mg][Mg] HZZOEADXZLYIHG-UHFFFAOYSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000861 pro-apoptotic effect Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 102000003702 retinoic acid receptors Human genes 0.000 description 1
- 108090000064 retinoic acid receptors Proteins 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LV060151A LV13735B (en) | 2006-12-28 | 2006-12-28 | Method for manufacturing substituted adamantylarylmagnesium chalogenides |
| EA200900899A EA015949B1 (ru) | 2006-12-28 | 2007-12-28 | Способ получения замещённых адамантиларилмагний галогенидов |
| EP07858234A EP2129679A2 (en) | 2006-12-28 | 2007-12-28 | A method for preparation of substituted adamantylarylmagnesium halides |
| UAA200907979A UA97507C2 (ru) | 2006-12-28 | 2007-12-28 | Способ получения замещенных адамантиларилмагниевых галидов |
| PCT/EP2007/064648 WO2008080993A2 (en) | 2006-12-28 | 2007-12-28 | A method for preparation of substituted adamantylarylmagnesium halides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LV060151A LV13735B (en) | 2006-12-28 | 2006-12-28 | Method for manufacturing substituted adamantylarylmagnesium chalogenides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LV13735B true LV13735B (en) | 2008-09-20 |
Family
ID=39589040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LV060151A LV13735B (en) | 2006-12-28 | 2006-12-28 | Method for manufacturing substituted adamantylarylmagnesium chalogenides |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2129679A2 (ru) |
| EA (1) | EA015949B1 (ru) |
| LV (1) | LV13735B (ru) |
| UA (1) | UA97507C2 (ru) |
| WO (1) | WO2008080993A2 (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113866292B (zh) * | 2021-09-13 | 2024-03-19 | 河北威远生物化工有限公司 | 一种邻氯苄基氯化镁含量的测定方法 |
| CN117511212B (zh) * | 2023-11-09 | 2024-04-12 | 东莞市好易达新材料科技有限公司 | 一种耐高温的硅树脂玻璃纤维套管和制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100348569C (zh) | 2001-11-30 | 2007-11-14 | 伯哈姆学院 | 癌细胞中编程性细胞死亡的诱导 |
| EP1582523A1 (en) | 2004-04-02 | 2005-10-05 | Ludwig-Maximilians-Universität München | Method of preparing organomagnesium compounds |
-
2006
- 2006-12-28 LV LV060151A patent/LV13735B/lv unknown
-
2007
- 2007-12-28 EA EA200900899A patent/EA015949B1/ru not_active IP Right Cessation
- 2007-12-28 UA UAA200907979A patent/UA97507C2/ru unknown
- 2007-12-28 WO PCT/EP2007/064648 patent/WO2008080993A2/en active Application Filing
- 2007-12-28 EP EP07858234A patent/EP2129679A2/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| UA97507C2 (ru) | 2012-02-27 |
| EP2129679A2 (en) | 2009-12-09 |
| EA015949B1 (ru) | 2011-12-30 |
| WO2008080993A3 (en) | 2009-03-12 |
| WO2008080993A2 (en) | 2008-07-10 |
| EA200900899A1 (ru) | 2010-02-26 |
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