SK16332002A3 - Spôsob prípravy bifenylových zlúčenín - Google Patents

Spôsob prípravy bifenylových zlúčenín Download PDF

Info

Publication number: SK16332002A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; water; mixture; acetone
Prior art date: 2000-05-19

Application number

SK1633-2002A

Other languages

English (en)

Slovak (sk)

Inventor

John Paul Gardner

William David Miller

Original Assignee

Eli Lilly And Company

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

2000-05-19

Filing date

2001-05-04

Publication date

2003-05-02

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22764479&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK16332002(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-05-04 Application filed by Eli Lilly And Company filed Critical Eli Lilly And Company

2003-05-02 Publication of SK16332002A3 publication Critical patent/SK16332002A3/sk

Links

ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims abstract description 14
238000004519 manufacturing process Methods 0.000 title 1
239000003960 organic solvent Substances 0.000 claims abstract description 40
-1 biphenyl compound Chemical class 0.000 claims abstract description 37
238000000034 method Methods 0.000 claims abstract description 37
238000002360 preparation method Methods 0.000 claims abstract description 25
239000003054 catalyst Substances 0.000 claims abstract description 15
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims abstract description 15
239000000654 additive Substances 0.000 claims abstract description 13
230000000996 additive effect Effects 0.000 claims abstract description 10
239000004305 biphenyl Substances 0.000 claims abstract description 8
235000010290 biphenyl Nutrition 0.000 claims abstract description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 75
150000001875 compounds Chemical class 0.000 claims description 70
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
239000000203 mixture Substances 0.000 claims description 43
239000000539 dimer Substances 0.000 claims description 35
239000011541 reaction mixture Substances 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 25
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 24
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
150000001555 benzenes Chemical class 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
239000004280 Sodium formate Substances 0.000 claims description 2
150000008424 iodobenzenes Chemical class 0.000 claims description 2
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical group [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
235000019254 sodium formate Nutrition 0.000 claims description 2
150000005171 halobenzenes Chemical class 0.000 abstract 1
239000000243 solution Substances 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 31
239000007787 solid Substances 0.000 description 30
150000003839 salts Chemical class 0.000 description 28
238000003756 stirring Methods 0.000 description 27
239000012074 organic phase Substances 0.000 description 25
239000000706 filtrate Substances 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
150000003456 sulfonamides Chemical class 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 16
239000008346 aqueous phase Substances 0.000 description 16
239000000460 chlorine Substances 0.000 description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
239000000725 suspension Substances 0.000 description 16
235000019441 ethanol Nutrition 0.000 description 15
235000019439 ethyl acetate Nutrition 0.000 description 14
238000001914 filtration Methods 0.000 description 14
239000002585 base Substances 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
229940124530 sulfonamide Drugs 0.000 description 12
150000003141 primary amines Chemical class 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
239000012071 phase Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
AXORVIZLPOGIRG-QMMMGPOBSA-N R-BETA-METHYLPHENYLETHYLAMINE Chemical compound NC[C@H](C)C1=CC=CC=C1 AXORVIZLPOGIRG-QMMMGPOBSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 8
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000012458 free base Substances 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 7
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
238000010992 reflux Methods 0.000 description 6
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000011630 iodine Substances 0.000 description 5
229940049920 malate Drugs 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
229940044613 1-propanol Drugs 0.000 description 4
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
239000005695 Ammonium acetate Substances 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
HKDGEKJGALNMPF-UHFFFAOYSA-N [4-[2-(methanesulfonamido)ethyl]phenyl]boronic acid Chemical compound CS(=O)(=O)NCCC1=CC=C(B(O)O)C=C1 HKDGEKJGALNMPF-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
235000019257 ammonium acetate Nutrition 0.000 description 4
229940043376 ammonium acetate Drugs 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
150000003840 hydrochlorides Chemical class 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
ALSHDGWOBNSWLZ-JTQLQIEISA-N n-[(2r)-2-(4-iodophenyl)propyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC[C@H](C)C1=CC=C(I)C=C1 ALSHDGWOBNSWLZ-JTQLQIEISA-N 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
HBVYOCJBEXSCQE-UHFFFAOYSA-N 2-phenylpropan-1-amine;hydrochloride Chemical compound Cl.NCC(C)C1=CC=CC=C1 HBVYOCJBEXSCQE-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000013058 crude material Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229940116298 l- malic acid Drugs 0.000 description 3
235000011090 malic acid Nutrition 0.000 description 3
JGDDFCYMSLNOGJ-UHFFFAOYSA-N n-(2-phenylethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCC1=CC=CC=C1 JGDDFCYMSLNOGJ-UHFFFAOYSA-N 0.000 description 3
HIYDOWJVBIJBQF-NSHDSACASA-N n-[(2r)-2-phenylpropyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC[C@H](C)C1=CC=CC=C1 HIYDOWJVBIJBQF-NSHDSACASA-N 0.000 description 3
NQTFJOYEXRRANY-UHFFFAOYSA-N n-[2-(4-iodophenyl)ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCC1=CC=C(I)C=C1 NQTFJOYEXRRANY-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000012552 review Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000002002 slurry Substances 0.000 description 3
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
PFRZSSVRWDNECD-UHFFFAOYSA-N tert-butyl n-[2-(4-iodophenyl)ethyl]-n-methylsulfonylcarbamate Chemical compound CC(C)(C)OC(=O)N(S(C)(=O)=O)CCC1=CC=C(I)C=C1 PFRZSSVRWDNECD-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
AXORVIZLPOGIRG-UHFFFAOYSA-N β-methylphenethylamine Chemical compound NCC(C)C1=CC=CC=C1 AXORVIZLPOGIRG-UHFFFAOYSA-N 0.000 description 3
BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
ATXDPYYMOTXKSG-UHFFFAOYSA-N CC(C)(C)ON(C(=O)S(C)(=O)=O)CCC1=CC=C(B(O)O)C=C1 Chemical compound CC(C)(C)ON(C(=O)S(C)(=O)=O)CCC1=CC=C(B(O)O)C=C1 ATXDPYYMOTXKSG-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000001099 ammonium carbonate Substances 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
150000001639 boron compounds Chemical class 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000005356 chiral GC Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
125000005207 tetraalkylammonium group Chemical group 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
NVAOLENBKNECGF-UHFFFAOYSA-N 2-phenylpropanenitrile Chemical compound N#CC(C)C1=CC=CC=C1 NVAOLENBKNECGF-UHFFFAOYSA-N 0.000 description 1
UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229910004003 H5IO6 Inorganic materials 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000872931 Myoporum sandwicense Species 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
MVFGXYPEQHIKIX-UHFFFAOYSA-N acetic acid;heptane Chemical compound CC(O)=O.CCCCCCC MVFGXYPEQHIKIX-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000006242 amine protecting group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000012538 ammonium bicarbonate Nutrition 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011324 bead Substances 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
AMJQWGIYCROUQF-UHFFFAOYSA-N calcium;methanolate Chemical compound [Ca+2].[O-]C.[O-]C AMJQWGIYCROUQF-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000006880 cross-coupling reaction Methods 0.000 description 1
230000001351 cycling effect Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
IIJREXIVDSIOFR-UHFFFAOYSA-N dichloromethane;heptane Chemical compound ClCCl.CCCCCCC IIJREXIVDSIOFR-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012039 electrophile Substances 0.000 description 1
238000003821 enantio-separation Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
JYGYEBCBALMPDC-UHFFFAOYSA-N heptane;propan-2-one Chemical compound CC(C)=O.CCCCCCC JYGYEBCBALMPDC-UHFFFAOYSA-N 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
PGXWDLGWMQIXDT-UHFFFAOYSA-N methylsulfinylmethane;hydrate Chemical compound O.CS(C)=O PGXWDLGWMQIXDT-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
TWLXDPFBEPBAQB-UHFFFAOYSA-N orthoperiodic acid Chemical compound OI(O)(O)(O)(O)=O TWLXDPFBEPBAQB-UHFFFAOYSA-N 0.000 description 1
BHIIWXJHALLFBD-UHFFFAOYSA-N oxolane;propan-2-ol Chemical compound CC(C)O.C1CCOC1 BHIIWXJHALLFBD-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
KIDBBTHHMJOMAU-UHFFFAOYSA-N propan-1-ol;hydrate Chemical compound O.CCCO KIDBBTHHMJOMAU-UHFFFAOYSA-N 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
PBEZJWDXAZCWKF-UHFFFAOYSA-N tert-butyl n-methylsulfonyl-n-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=CC(CCN(C(=O)OC(C)(C)C)S(C)(=O)=O)=CC=C1B1OC(C)(C)C(C)(C)O1 PBEZJWDXAZCWKF-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK1633-2002A 2000-05-19 2001-05-04 Spôsob prípravy bifenylových zlúčenín SK16332002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US20598200P	2000-05-19	2000-05-19
PCT/US2001/011745 WO2001090055A2 (en)	2000-05-19	2001-05-04	A process for preparing biphenyl compounds

Publications (1)

Publication Number	Publication Date
SK16332002A3 true SK16332002A3 (sk)	2003-05-02

Family

ID=22764479

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1633-2002A SK16332002A3 (sk)	2000-05-19	2001-05-04	Spôsob prípravy bifenylových zlúčenín

Country Status (26)

Country	Link
EP (1)	EP1294683B1 (de)
JP (1)	JP2003534314A (de)
KR (1)	KR20030007635A (de)
CN (2)	CN1219756C (de)
AR (1)	AR028589A1 (de)
AT (1)	ATE311362T1 (de)
AU (2)	AU5905201A (de)
BR (1)	BR0110782A (de)
CA (1)	CA2409824A1 (de)
CZ (1)	CZ20023636A3 (de)
DE (1)	DE60115444T2 (de)
EA (1)	EA200201233A1 (de)
EC (1)	ECSP014080A (de)
ES (1)	ES2249433T3 (de)
HR (1)	HRP20020919A2 (de)
HU (1)	HUP0302246A2 (de)
IL (1)	IL152159A0 (de)
MX (1)	MXPA02011306A (de)
NO (1)	NO20025465L (de)
NZ (1)	NZ521475A (de)
PE (1)	PE20020113A1 (de)
PL (1)	PL362893A1 (de)
SK (1)	SK16332002A3 (de)
SV (1)	SV2002000457A (de)
WO (1)	WO2001090055A2 (de)
ZA (1)	ZA200209368B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9702194D0 (en)	1997-02-04	1997-03-26	Lilly Co Eli	Sulphonide derivatives
JP2004503527A (ja)	2000-06-13	2004-02-05	イーライ・リリー・アンド・カンパニー	スルホンアミド誘導体
AR052930A1 (es) *	2005-03-02	2007-04-11	Basf Ag	Procedimiento para la preparacion de bifenilos sustituidos
JP2007106697A (ja) *	2005-10-13	2007-04-26	Sederma Sa	新規なチラミン誘導体及びその製造方法、並びに該誘導体を含む化粧用組成物、若しくは皮膚用医薬組成物
AU2006327300A1 (en)	2005-12-20	2007-06-28	Astrazeneca Ab	Substituted Cinnoline derivatives as GABAa-receptor modulators and method for their synthesis
US7465795B2 (en)	2005-12-20	2008-12-16	Astrazeneca Ab	Compounds and uses thereof
AP3066A (en)	2009-06-26	2014-12-31	Pfizer	Heterocyclic sulfonamides, uses and pharmaceuticalcompositions thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6525099B1 (en) *	1998-07-31	2003-02-25	Eli Lilly And Company	N-substituted sulfonamide derivatives

2001
- 2001-05-04 DE DE60115444T patent/DE60115444T2/de not_active Expired - Fee Related
- 2001-05-04 AT AT01932535T patent/ATE311362T1/de not_active IP Right Cessation
- 2001-05-04 CN CNB018096662A patent/CN1219756C/zh not_active Expired - Fee Related
- 2001-05-04 ES ES01932535T patent/ES2249433T3/es not_active Expired - Lifetime
- 2001-05-04 CN CNA2004100119229A patent/CN1769266A/zh active Pending
- 2001-05-04 JP JP2001586245A patent/JP2003534314A/ja not_active Withdrawn
- 2001-05-04 HU HU0302246A patent/HUP0302246A2/hu unknown
- 2001-05-04 MX MXPA02011306A patent/MXPA02011306A/es not_active Application Discontinuation
- 2001-05-04 CZ CZ20023636A patent/CZ20023636A3/cs unknown
- 2001-05-04 PL PL01362893A patent/PL362893A1/xx unknown
- 2001-05-04 WO PCT/US2001/011745 patent/WO2001090055A2/en not_active Ceased
- 2001-05-04 HR HR20020919A patent/HRP20020919A2/hr not_active Application Discontinuation
- 2001-05-04 AU AU5905201A patent/AU5905201A/xx active Pending
- 2001-05-04 AU AU2001259052A patent/AU2001259052B2/en not_active Expired - Fee Related
- 2001-05-04 NZ NZ521475A patent/NZ521475A/en not_active Application Discontinuation
- 2001-05-04 CA CA002409824A patent/CA2409824A1/en not_active Abandoned
- 2001-05-04 KR KR1020027015473A patent/KR20030007635A/ko not_active Withdrawn
- 2001-05-04 BR BR0110782-8A patent/BR0110782A/pt not_active IP Right Cessation
- 2001-05-04 SK SK1633-2002A patent/SK16332002A3/sk not_active Application Discontinuation
- 2001-05-04 IL IL15215901A patent/IL152159A0/xx unknown
- 2001-05-04 EP EP01932535A patent/EP1294683B1/de not_active Revoked
- 2001-05-04 EA EA200201233A patent/EA200201233A1/ru unknown
- 2001-05-18 SV SV2001000457A patent/SV2002000457A/es not_active Application Discontinuation
- 2001-05-18 EC EC2001004080A patent/ECSP014080A/es unknown
- 2001-05-18 AR ARP010102375A patent/AR028589A1/es not_active Application Discontinuation
- 2001-05-18 PE PE2001000453A patent/PE20020113A1/es not_active Application Discontinuation
2002
- 2002-11-14 NO NO20025465A patent/NO20025465L/no not_active Application Discontinuation
- 2002-11-18 ZA ZA200209368A patent/ZA200209368B/en unknown

Also Published As

Publication number	Publication date
CN1219756C (zh)	2005-09-21
HUP0302246A2 (hu)	2003-10-28
NZ521475A (en)	2004-04-30
BR0110782A (pt)	2003-05-13
JP2003534314A (ja)	2003-11-18
NO20025465D0 (no)	2002-11-14
KR20030007635A (ko)	2003-01-23
EA200201233A1 (ru)	2003-04-24
PL362893A1 (en)	2004-11-02
WO2001090055A3 (en)	2002-04-11
AR028589A1 (es)	2003-05-14
IL152159A0 (en)	2003-05-29
AU5905201A (en)	2001-12-03
ES2249433T3 (es)	2006-04-01
DE60115444T2 (de)	2006-07-27
CN1429204A (zh)	2003-07-09
ATE311362T1 (de)	2005-12-15
MXPA02011306A (es)	2003-04-25
WO2001090055A2 (en)	2001-11-29
PE20020113A1 (es)	2002-02-21
ECSP014080A (es)	2002-02-25
CZ20023636A3 (cs)	2003-02-12
HRP20020919A2 (en)	2004-02-29
DE60115444D1 (de)	2006-01-05
ZA200209368B (en)	2003-11-18
NO20025465L (no)	2003-01-20
SV2002000457A (es)	2002-07-03
CN1769266A (zh)	2006-05-10
EP1294683A2 (de)	2003-03-26
EP1294683B1 (de)	2005-11-30
CA2409824A1 (en)	2001-11-29
AU2001259052B2 (en)	2006-03-02

Legal Events

Date	Code	Title	Description
2010-08-09	FC9A	Refused patent application

Publication	Publication Date	Title
PT2477992T (pt)	2017-03-20	Processos para a preparação de darunavir e a forma amorfa do mesmo
WO2011117393A1 (en)	2011-09-29	Racemisation of (r)-n-boc-3-hydroxyadamant-1-yl glycine
SK16332002A3 (sk)	2003-05-02	Spôsob prípravy bifenylových zlúčenín
JPWO2001094304A1 (ja)	2003-08-12	スルホン酸エステルの製造方法
AU2001259052A1 (en)	2002-02-21	A process for preparing biphenyl compounds
US8835684B2 (en)	2014-09-16	Preparation of 2R,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines
US6984756B2 (en)	2006-01-10	Process for preparing biphenyl compounds
JP5305593B2 (ja)	2013-10-02	高化学的ｒ−５−（２−（２−エトキシフェノキシエチルアミノ）プロピル）−２−メトキシベンゼンスルホンアミド塩酸塩の調製
EP1244610B1 (de)	2008-07-16	Verbessertes verfahren zur herstellung von 2s,3s-n-isobutyl-n-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamid hydrochlorid und anderen derivaten von 2-hydroxy-1,3-diamin
JPWO2002018403A1 (ja)	2003-10-21	エリスロマイシン誘導体の製造方法
US20050032889A1 (en)	2005-02-10	Process for producing crystal of benzenesulfonamide derivative, and novel crystal of intermediate therefor and process for producing the same
US8273918B2 (en)	2012-09-25	Process for preparing tamsulosin hydrochloride
WO2025008772A2 (en)	2025-01-09	Improved manufacturing process and intermediates for a pyrrolo[2,3-d]pyrimidine compound and use thereof
JP2004238322A (ja)	2004-08-26	（ｒ）−３−アミノペンタンニトリルメタンスルホン酸塩の製造方法
JP2002255932A (ja)	2002-09-11	３−アルキルアミノアゼチジンの製造方法
JP2953553B2 (ja)	1999-09-27	Ｎ−アルコキシカルボニルアミノ酸エステルの製造方法
WO2019098551A1 (ko)	2019-05-23	의약품 합성용 중간체 화합물의 제조 방법