SA99191000A - طريقة لتحضير احماض مستبدل 4-فنيل-4-سيانو سيكلو هكسانويك - Google Patents

طريقة لتحضير احماض مستبدل 4-فنيل-4-سيانو سيكلو هكسانويك Download PDF

Info

Publication number: SA99191000A
Authority: SA; Saudi Arabia
Prior art keywords: group; lithium; water; elements; substituted
Prior art date: 1997-10-10

Application number

SA99191000A

Other languages

Arabic (ar)

English (en)

Inventor

جيانهاو شين

كيفن ويب

ولفورد مينديلسون

Original Assignee

سميثكلاين بيتشام كوربوريشن

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.)

1997-10-10

Filing date

1999-01-26

Publication date

2005-12-03

1999-01-26 Application filed by سميثكلاين بيتشام كوربوريشن filed Critical سميثكلاين بيتشام كوربوريشن

2005-12-03 Publication of SA99191000A publication Critical patent/SA99191000A/ar

Links

238000000034 method Methods 0.000 title claims abstract description 28
239000002253 acid Substances 0.000 title claims description 22
150000007513 acids Chemical class 0.000 title description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 46
239000002904 solvent Substances 0.000 claims abstract description 24
150000001875 compounds Chemical class 0.000 claims abstract description 20
150000001408 amides Chemical class 0.000 claims abstract description 13
150000005309 metal halides Chemical class 0.000 claims abstract description 12
229910001507 metal halide Inorganic materials 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims description 45
238000006243 chemical reaction Methods 0.000 claims description 21
-1 methyl hydroxyl Chemical group 0.000 claims description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
239000000047 product Substances 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 12
239000002244 precipitate Substances 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052744 lithium Inorganic materials 0.000 claims description 8
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
150000004820 halides Chemical class 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
238000000746 purification Methods 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 2
229910001623 magnesium bromide Inorganic materials 0.000 claims description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims description 2
238000001556 precipitation Methods 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
229910052614 beryl Inorganic materials 0.000 claims 1
150000007942 carboxylates Chemical class 0.000 claims 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000001145 hydrido group Chemical group *[H] 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 claims 1
229910001947 lithium oxide Inorganic materials 0.000 claims 1
JFRJCQJVFMHZOO-QZHHGCDDSA-N n-(2-aminoethyl)-2-[4-[[2-[4-[[9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]phenyl]acetyl]amino]phenyl]acetamide Chemical compound C1=CC(CC(=O)NCCN)=CC=C1NC(=O)CC(C=C1)=CC=C1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 JFRJCQJVFMHZOO-QZHHGCDDSA-N 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
230000021523 carboxylation Effects 0.000 abstract 1
238000006473 carboxylation reaction Methods 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
238000004821 distillation Methods 0.000 description 18
150000003839 salts Chemical class 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 13
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
239000012071 phase Substances 0.000 description 11
238000007792 addition Methods 0.000 description 10
230000000694 effects Effects 0.000 description 10
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 6
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 6
208000006673 asthma Diseases 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000005406 washing Methods 0.000 description 6
210000004027 cell Anatomy 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
230000003993 interaction Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
102000030621 adenylate cyclase Human genes 0.000 description 3
108060000200 adenylate cyclase Proteins 0.000 description 3
230000009286 beneficial effect Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910003002 lithium salt Inorganic materials 0.000 description 3
159000000002 lithium salts Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
210000003739 neck Anatomy 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000037361 pathway Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
230000009466 transformation Effects 0.000 description 3
ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
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108010044467 Isoenzymes Proteins 0.000 description 2
108010010677 Phosphodiesterase I Proteins 0.000 description 2
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000003322 aneuploid effect Effects 0.000 description 2
208000036878 aneuploidy Diseases 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
NDTCXABJQNJPCF-UHFFFAOYSA-N chlorocyclopentane Chemical compound ClC1CCCC1 NDTCXABJQNJPCF-UHFFFAOYSA-N 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
229940095074 cyclic amp Drugs 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
238000005469 granulation Methods 0.000 description 2
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239000005556 hormone Substances 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
210000004969 inflammatory cell Anatomy 0.000 description 2
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229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
210000001616 monocyte Anatomy 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
150000003891 oxalate salts Chemical class 0.000 description 2
230000007310 pathophysiology Effects 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
YYGXWGFETIURIJ-UHFFFAOYSA-N 1,4-dioxane;sodium Chemical compound [Na].C1COCCO1 YYGXWGFETIURIJ-UHFFFAOYSA-N 0.000 description 1
XWFKZQVEYDVFTA-UHFFFAOYSA-N 4-cyano-4-phenylcyclohexane-1-carboxylic acid Chemical class C1CC(C(=O)O)CCC1(C#N)C1=CC=CC=C1 XWFKZQVEYDVFTA-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000002126 C01EB10 - Adenosine Substances 0.000 description 1
101100416200 Caenorhabditis elegans rla-0 gene Proteins 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
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101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 description 1
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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230000003213 activating effect Effects 0.000 description 1
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229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
210000003651 basophil Anatomy 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
230000008512 biological response Effects 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
AFDBQQUMYHWKNQ-UHFFFAOYSA-N calcium;strontium Chemical compound [Ca+2].[Sr] AFDBQQUMYHWKNQ-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
208000023819 chronic asthma Diseases 0.000 description 1
239000005515 coenzyme Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
210000002745 epiphysis Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000004673 fluoride salts Chemical group 0.000 description 1
229910052730 francium Inorganic materials 0.000 description 1
KLMCZVJOEAUDNE-UHFFFAOYSA-N francium atom Chemical compound [Fr] KLMCZVJOEAUDNE-UHFFFAOYSA-N 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
JEGUKCSWCFPDGT-UHFFFAOYSA-M hydroxide;hydrate Chemical compound O.[OH-] JEGUKCSWCFPDGT-UHFFFAOYSA-M 0.000 description 1
208000013403 hyperactivity Diseases 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910001853 inorganic hydroxide Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
125000003473 lipid group Chemical group 0.000 description 1
FZRNJOXQNWVMIH-UHFFFAOYSA-N lithium;hydrate Chemical compound [Li].O FZRNJOXQNWVMIH-UHFFFAOYSA-N 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005272 metallurgy Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
DKSBQEIJEJFTAW-UHFFFAOYSA-N methanol N-methylformamide Chemical compound CO.CNC=O DKSBQEIJEJFTAW-UHFFFAOYSA-N 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000004712 monophosphates Chemical class 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
125000005592 polycycloalkyl group Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pulmonology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SA99191000A 1997-10-10 1999-01-26 طريقة لتحضير احماض مستبدل 4-فنيل-4-سيانو سيكلو هكسانويك SA99191000A (ar)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US6161397P	1997-10-10	1997-10-10

Publications (1)

Publication Number	Publication Date
SA99191000A true SA99191000A (ar)	2005-12-03

Family

ID=22036929

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SA99191000A SA99191000A (ar)	1997-10-10	1999-01-26	طريقة لتحضير احماض مستبدل 4-فنيل-4-سيانو سيكلو هكسانويك

Country Status (30)

Country	Link
EP (1)	EP1043930A4 (id)
JP (1)	JP2001519363A (id)
KR (1)	KR100560038B1 (id)
CN (1)	CN1192025C (id)
AP (1)	AP1335A (id)
AR (1)	AR015952A1 (id)
AU (1)	AU741832B2 (id)
BG (1)	BG104302A (id)
BR (1)	BR9814064A (id)
CA (1)	CA2305614A1 (id)
DZ (1)	DZ2619A1 (id)
EA (1)	EA003609B1 (id)
HU (1)	HUP0003905A3 (id)
ID (1)	ID25536A (id)
IL (1)	IL135434A (id)
MA (1)	MA24670A1 (id)
MY (1)	MY122105A (id)
NO (1)	NO20001777L (id)
NZ (1)	NZ503759A (id)
OA (1)	OA11347A (id)
PE (1)	PE121599A1 (id)
PL (1)	PL191974B1 (id)
SA (1)	SA99191000A (id)
SK (1)	SK4902000A3 (id)
TR (1)	TR200000945T2 (id)
TW (1)	TW440557B (id)
UA (1)	UA67753C2 (id)
UY (2)	UY25201A1 (id)
WO (1)	WO1999018793A1 (id)
ZA (1)	ZA989228B (id)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9920152D0 (en) *	1999-08-25	1999-10-27	Smithkline Beecham Plc	Novel process
EP1237851A4 (en) *	1999-12-15	2004-06-23	Smithkline Beecham	SALES OF I CIS / I-4-CYANO-4-3- (CYCLOPENTYLOXY) -4-METHOXYPHENYL] CYCLHEXAN-1-CARBONIC ACID
EP1250313B1 (en) *	2000-01-26	2006-11-02	SmithKline Beecham Corporation	Monohydrate of cis-lithium-cyano-4- 3-(cyclopentyloxy)-4-methoxyphenyl\|cyclohexanecarboxylate
WO2001068600A2 (en)	2000-03-16	2001-09-20	Inflazyme Pharmaceuticals Limited	Benzylated pde4 inhibitors
KR20030070150A (ko)	2001-01-31	2003-08-27	화이자 프로덕츠 인크.	Ｐｄｅ4 이소자임 억제제로서 유용한 에테르 유도체
OA12542A (en)	2001-01-31	2006-06-05	Pfizer Prod Inc	Thiazolyl-, oxazolyl-, pyrrolyl-, and imidazolyl-acid amide derivatives useful as inhibitors of PDE4isozymes.
US7250518B2 (en)	2001-01-31	2007-07-31	Pfizer Inc.	Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes
JP2004520386A (ja)	2001-01-31	2004-07-08	ファイザー・プロダクツ・インク	Ｐｄｅ４アイソザイムの阻害剤として有用なニコチンアミドビアリール誘導体
CN102491959B (zh) *	2011-12-19	2015-03-25	江苏澄扬作物科技有限公司	一种环氧乙烷衍生物的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4021478A (en) *	1972-07-13	1977-05-03	The Upjohn Company	Preparation of carboxylic acids from glycidonitriles with ionic lewis acids
HU225869B1 (en) *	1992-04-02	2007-11-28	Smithkline Beecham Corp	Compounds with antiallergic and antiinflammatory activity and pharmaceutical compns. contg. them
US5524438A (en) *	1994-12-15	1996-06-11	United Technologies Corporation	Segmented bulkhead liner for a gas turbine combustor
UY24882A1 (es) *	1997-02-12	2001-08-27	Smithkline Beecham Corp	Ácidos 4-fenil-4-ciano-ciclohexanoicos sustituidos
US6452022B1 (en) *	1997-10-10	2002-09-17	Smithkline Beecham Corporation	Method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids

1998
- 1998-07-10 UA UA2000041944A patent/UA67753C2/uk unknown
- 1998-10-02 MA MA25278A patent/MA24670A1/fr unknown
- 1998-10-07 AP APAP/P/2000/001782A patent/AP1335A/en active
- 1998-10-07 CA CA002305614A patent/CA2305614A1/en not_active Abandoned
- 1998-10-07 PL PL339759A patent/PL191974B1/pl not_active IP Right Cessation
- 1998-10-07 JP JP2000515437A patent/JP2001519363A/ja active Pending
- 1998-10-07 WO PCT/US1998/021061 patent/WO1999018793A1/en not_active Ceased
- 1998-10-07 UY UY25201A patent/UY25201A1/es not_active IP Right Cessation
- 1998-10-07 NZ NZ503759A patent/NZ503759A/en unknown
- 1998-10-07 SK SK490-2000A patent/SK4902000A3/sk unknown
- 1998-10-07 HU HU0003905A patent/HUP0003905A3/hu not_active Application Discontinuation
- 1998-10-07 ID IDW20000614A patent/ID25536A/id unknown
- 1998-10-07 TR TR2000/00945T patent/TR200000945T2/xx unknown
- 1998-10-07 AU AU96874/98A patent/AU741832B2/en not_active Ceased
- 1998-10-07 CN CNB988100304A patent/CN1192025C/zh not_active Expired - Fee Related
- 1998-10-07 BR BR9814064-7A patent/BR9814064A/pt not_active IP Right Cessation
- 1998-10-07 EA EA200000406A patent/EA003609B1/ru not_active IP Right Cessation
- 1998-10-07 KR KR1020007003742A patent/KR100560038B1/ko not_active Expired - Fee Related
- 1998-10-07 EP EP98950965A patent/EP1043930A4/en not_active Withdrawn
- 1998-10-07 IL IL13543498A patent/IL135434A/en not_active IP Right Cessation
- 1998-10-07 DZ DZ980229A patent/DZ2619A1/xx active
- 1998-10-07 AR ARP980105002A patent/AR015952A1/es unknown
- 1998-10-08 MY MYPI98004606A patent/MY122105A/en unknown
- 1998-10-09 PE PE1998000955A patent/PE121599A1/es not_active Application Discontinuation
- 1998-10-09 ZA ZA989228A patent/ZA989228B/xx unknown
- 1998-12-01 TW TW087116680A patent/TW440557B/zh not_active IP Right Cessation
1999
- 1999-01-26 SA SA99191000A patent/SA99191000A/ar unknown
- 1999-05-25 UY UY25524A patent/UY25524A1/es not_active Application Discontinuation
2000
- 2000-04-05 BG BG104302A patent/BG104302A/xx unknown
- 2000-04-06 NO NO20001777A patent/NO20001777L/no not_active Application Discontinuation
- 2000-04-07 OA OA1200000100A patent/OA11347A/en unknown

Also Published As

Publication number	Publication date
ID25536A (id)	2000-10-12
UY25524A1 (es)	2000-02-23
AP2000001782A0 (en)	2000-06-30
DZ2619A1 (fr)	2003-03-08
PE121599A1 (es)	2000-02-19
UY25201A1 (es)	2001-08-27
AU741832B2 (en)	2001-12-13
IL135434A0 (en)	2001-05-20
NO20001777D0 (no)	2000-04-06
WO1999018793A1 (en)	1999-04-22
NZ503759A (en)	2002-03-01
CN1192025C (zh)	2005-03-09
EA200000406A1 (ru)	2000-10-30
NO20001777L (no)	2000-05-03
PL339759A1 (en)	2001-01-02
KR20010015709A (ko)	2001-02-26
HUP0003905A3 (en)	2002-01-28
JP2001519363A (ja)	2001-10-23
BR9814064A (pt)	2000-09-26
SK4902000A3 (en)	2000-11-07
AU9687498A (en)	1999-05-03
CA2305614A1 (en)	1999-04-22
AP1335A (en)	2004-11-29
OA11347A (en)	2003-12-17
MY122105A (en)	2006-03-31
EA003609B1 (ru)	2003-06-26
BG104302A (en)	2001-08-31
MA24670A1 (fr)	1999-07-01
HUP0003905A2 (en)	2001-03-28
CN1275052A (zh)	2000-11-29
UA67753C2 (uk)	2004-07-15
EP1043930A1 (en)	2000-10-18
EP1043930A4 (en)	2004-09-15
TR200000945T2 (tr)	2000-10-23
KR100560038B1 (ko)	2006-03-13
PL191974B1 (pl)	2006-07-31
AR015952A1 (es)	2001-05-30
IL135434A (en)	2004-12-15
TW440557B (en)	2001-06-16
ZA989228B (en)	1999-04-12

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