NO328548B1 - Nye mandelatsalter av substituerte tetracykliske tetrahydrofuranderivater - Google Patents

Nye mandelatsalter av substituerte tetracykliske tetrahydrofuranderivater Download PDF

Info

Publication number: NO328548B1
Authority: NO; Norway
Prior art keywords: mandelate salt; dibenzo; furan; tetrahydro; cyclohepta
Prior art date: 2001-11-09

Application number

NO20041848A

Other languages

English (en)

Norwegian (no)

Other versions

NO20041848L (no

Inventor

Johannes Josephus Maria Willems

Bart Petrus Anna Maria Jozef Medaer

Sigrid Carl Maria Stokbroekx

Yves Georges Ruysschaert

Johan Erwin Edmond Weerts

Original Assignee

Janssen Pharmaceutica Nv

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.)

2001-11-09

Filing date

2004-05-05

Publication date

2010-03-15

2004-05-05 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2004-05-05 Publication of NO20041848L publication Critical patent/NO20041848L/no

2010-03-15 Publication of NO328548B1 publication Critical patent/NO328548B1/no

Links

150000003839 salts Chemical class 0.000 title description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title description 12
210000004373 mandible Anatomy 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 52
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical class [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims description 47
239000002904 solvent Substances 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
208000028017 Psychotic disease Diseases 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 4
208000019695 Migraine disease Diseases 0.000 claims description 4
230000036506 anxiety Effects 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
206010027599 migraine Diseases 0.000 claims description 4
201000000980 schizophrenia Diseases 0.000 claims description 4
208000019116 sleep disease Diseases 0.000 claims description 4
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229960002510 mandelic acid Drugs 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000001953 recrystallisation Methods 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
238000001816 cooling Methods 0.000 claims description 2
239000002178 crystalline material Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
238000007670 refining Methods 0.000 claims 1
239000000543 intermediate Substances 0.000 description 36
239000000243 solution Substances 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
-1 for example Chemical group 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
239000002253 acid Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
238000003860 storage Methods 0.000 description 7
150000003892 tartrate salts Chemical class 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000001860 citric acid derivatives Chemical class 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000007962 solid dispersion Substances 0.000 description 6
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 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
238000002336 sorption--desorption measurement Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000035945 sensitivity Effects 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
GNBSFNIPZPZGCX-UHFFFAOYSA-N 2h-cyclohepta[b]furan-2-ylmethanamine Chemical compound C1=CC=CC2=CC(CN)OC2=C1 GNBSFNIPZPZGCX-UHFFFAOYSA-N 0.000 description 3
229920000858 Cyclodextrin Polymers 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
150000001204 N-oxides Chemical group 0.000 description 3
241000700159 Rattus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
ZWJMXJUZYGTMSZ-UHFFFAOYSA-N bis(2-methylbenzoyl) 2,3-dihydroxybutanedioate Chemical class CC1=CC=CC=C1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1C ZWJMXJUZYGTMSZ-UHFFFAOYSA-N 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
208000015114 central nervous system disease Diseases 0.000 description 3
230000008859 change Effects 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
239000000356 contaminant Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000002245 particle Substances 0.000 description 3
230000002265 prevention Effects 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000006104 solid solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
229920003169 water-soluble polymer Polymers 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
244000144725 Amygdalus communis Species 0.000 description 2
235000011437 Amygdalus communis Nutrition 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
208000018522 Gastrointestinal disease Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
238000004566 IR spectroscopy Methods 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
208000006011 Stroke Diseases 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
235000020224 almond Nutrition 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229940097362 cyclodextrins Drugs 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000003795 desorption Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
230000006870 function Effects 0.000 description 2
239000008103 glucose Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
150000002690 malonic acid derivatives Chemical class 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000006186 oral dosage form Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
208000020016 psychiatric disease Diseases 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000010956 selective crystallization Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
150000003890 succinate salts Chemical class 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
238000002411 thermogravimetry Methods 0.000 description 2
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 1
WMJNKBXKYHXOHC-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylbenzoyl)butanedioic acid Chemical class CC1=CC=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=CC=C1C WMJNKBXKYHXOHC-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
108091005479 5-HT2 receptors Proteins 0.000 description 1
102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 1
102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 1
LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
229940000681 5-hydroxytryptophan Drugs 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
208000020925 Bipolar disease Diseases 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
206010012335 Dependence Diseases 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
101150104779 HTR2A gene Proteins 0.000 description 1
101150013372 Htr2c gene Proteins 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
208000026139 Memory disease Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
208000019430 Motor disease Diseases 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
208000027626 Neurocognitive disease Diseases 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
206010033664 Panic attack Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
206010041250 Social phobia Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004974 alkaline earth metal peroxides Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000002282 antimigraine agent Substances 0.000 description 1
229940125684 antimigraine agent Drugs 0.000 description 1
239000000164 antipsychotic agent Substances 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000006399 behavior Effects 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
235000015895 biscuits Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000010568 chiral column chromatography Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
238000001938 differential scanning calorimetry curve Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
210000005095 gastrointestinal system Anatomy 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229960004337 hydroquinone Drugs 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000004899 motility Effects 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
230000004770 neurodegeneration Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
208000022821 personality disease Diseases 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000008569 process Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
208000012201 sexual and gender identity disease Diseases 0.000 description 1
208000015891 sexual disease Diseases 0.000 description 1
238000005055 short column chromatography Methods 0.000 description 1
208000022925 sleep disturbance Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000012430 stability testing Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Addiction (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Furan Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO20041848A 2001-11-09 2004-05-05 Nye mandelatsalter av substituerte tetracykliske tetrahydrofuranderivater NO328548B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01204465		2001-11-09
PCT/EP2002/011136 WO2003040122A1 (fr)	2001-11-09	2002-11-08	Nouveaux sels mandelates de derives de tetrahydrofuranes tetracycliques substitues

Publications (2)

Publication Number	Publication Date
NO20041848L NO20041848L (no)	2004-05-05
NO328548B1 true NO328548B1 (no)	2010-03-15

Family

ID=8181272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20041848A NO328548B1 (no)	2001-11-09	2004-05-05	Nye mandelatsalter av substituerte tetracykliske tetrahydrofuranderivater

Country Status (25)

Country	Link
US (1)	US7317115B2 (fr)
EP (1)	EP1446397B1 (fr)
JP (1)	JP2005508988A (fr)
KR (1)	KR100962325B1 (fr)
CN (1)	CN1582282B (fr)
AR (1)	AR037285A1 (fr)
AT (1)	ATE299138T1 (fr)
AU (1)	AU2002349327B2 (fr)
BR (1)	BR0212770A (fr)
CA (1)	CA2465043C (fr)
DE (1)	DE60204982T2 (fr)
EA (1)	EA006980B1 (fr)
ES (1)	ES2244818T3 (fr)
HR (1)	HRP20040395A2 (fr)
HU (1)	HUP0402224A3 (fr)
IL (2)	IL161866A0 (fr)
MX (1)	MXPA04004365A (fr)
MY (1)	MY128237A (fr)
NO (1)	NO328548B1 (fr)
NZ (1)	NZ531739A (fr)
PL (1)	PL368456A1 (fr)
TW (1)	TW200407117A (fr)
UA (1)	UA79248C2 (fr)
WO (1)	WO2003040122A1 (fr)
ZA (1)	ZA200403454B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2335700A1 (fr)	2001-07-25	2011-06-22	Boehringer Ingelheim (Canada) Ltd.	Inhibiteurs de la polymerase du virus hepatitis C avec une structure heterobicylic
KR20050044329A (ko) *	2001-12-07	2005-05-12	얀센 파마슈티카 엔.브이.	트랜스-융합된3,3ａ,8,12ｂ-테트라히드로-2Ｈ-디벤조[3,4:6,7]시클로헵타[1,2-ｂ]푸란 유도체의 제조
WO2005013969A1 (fr) *	2003-07-15	2005-02-17	Janssen Pharmaceutica N.V.	Agent antipsychotique a proprietes favorisant la socialisation
JP4912320B2 (ja)	2004-12-07	2012-04-11	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	置換された四環式テトラヒドロピラン、ピロリジンおよびテトラヒドロチオフェン誘導体
CA2595170C (fr)	2005-01-27	2014-08-05	Janssen Pharmaceutica N.V.	Derives heterocycliques tetracycliques de tetrahydrofuranne en tant qu'inhibiteurs de 5ht2 dans le traitement de troubles du systeme nerveux central
NZ564181A (en)	2005-06-17	2010-02-26	Janssen Pharmaceutica Nv	Novel tetracyclic tetrahydrofuran derivatives containing a cyclic amine side chain
US8507040B2 (en)	2008-05-08	2013-08-13	Air Products And Chemicals, Inc.	Binary and ternary metal chalcogenide materials and method of making and using same
US8765223B2 (en) *	2008-05-08	2014-07-01	Air Products And Chemicals, Inc.	Binary and ternary metal chalcogenide materials and method of making and using same
US8962675B1 (en) *	2013-09-12	2015-02-24	Abbvie Inc.	Atrasentan mandelate salts

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3644462A1 (de)	1986-12-24	1988-07-07	Basf Ag	Verfahren zur herstellung von 5h-dibenzo(a,d)cyclohepten-5-onen
JP2656720B2 (ja) *	1992-12-09	1997-09-24	武田薬品工業株式会社	光学活性アミノクマラン誘導体
WO1995025102A1 (fr) *	1994-03-16	1995-09-21	Novo Nordisk A/S	Sels d'addition d'acide de composes de 2,3,4,5-tetrahydro-1h-3-benzazepine
ES2196328T3 (es) *	1996-04-12	2003-12-16	Janssen Pharmaceutica Nv	Derivados de tetrahidrofurano tetraciclicos sustituidos.
WO1997044014A1 (fr)	1996-05-20	1997-11-27	Janssen Pharmaceutica N.V.	Compositions antifongiques avec biodisponibilite amelioree
UA52778C2 (uk) *	1997-10-10	2003-01-15	Янссен Фармацевтика Н.В.	Галогенозаміщені тетрациклічні похідні тетрагідрофурану, спосіб їх отримання та композиція на їх основі
US6281247B1 (en) *	1998-03-03	2001-08-28	Novo Nordisk A/S	Salt forms of (2E)-5-amino-5-methylhex-2-enoic acid N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)amide
HUP9904624A2 (hu) *	1999-12-17	2002-01-28	Sanofi-Synthelabo	Szacharinszármazékok, eljárás előállításukra, az ezeket tartalmazó gyógyszerkészítmények és intermedierjeik
EP1186303A3 (fr) *	2000-09-06	2003-12-10	Pfizer Products Inc.	Combinaisons pharmaceutiques pour le traitement des accidents cerebrovasculaires, contenant un facteur inhibitant la neutrophile et un antagoniste selectif du NMDA-NR2B

2002
- 2002-08-11 UA UA20040604168A patent/UA79248C2/uk unknown
- 2002-11-07 MY MYPI20024166A patent/MY128237A/en unknown
- 2002-11-08 CN CN02821918XA patent/CN1582282B/zh not_active Expired - Fee Related
- 2002-11-08 TW TW091132840A patent/TW200407117A/zh unknown
- 2002-11-08 IL IL16186602A patent/IL161866A0/xx unknown
- 2002-11-08 AT AT02781214T patent/ATE299138T1/de not_active IP Right Cessation
- 2002-11-08 NZ NZ531739A patent/NZ531739A/en not_active IP Right Cessation
- 2002-11-08 HR HR20040395A patent/HRP20040395A2/hr not_active Application Discontinuation
- 2002-11-08 EA EA200400656A patent/EA006980B1/ru not_active IP Right Cessation
- 2002-11-08 DE DE60204982T patent/DE60204982T2/de not_active Expired - Lifetime
- 2002-11-08 HU HU0402224A patent/HUP0402224A3/hu unknown
- 2002-11-08 EP EP02781214A patent/EP1446397B1/fr not_active Expired - Lifetime
- 2002-11-08 JP JP2003542168A patent/JP2005508988A/ja active Pending
- 2002-11-08 AU AU2002349327A patent/AU2002349327B2/en not_active Ceased
- 2002-11-08 WO PCT/EP2002/011136 patent/WO2003040122A1/fr not_active Ceased
- 2002-11-08 BR BR0212770-9A patent/BR0212770A/pt not_active IP Right Cessation
- 2002-11-08 ES ES02781214T patent/ES2244818T3/es not_active Expired - Lifetime
- 2002-11-08 MX MXPA04004365A patent/MXPA04004365A/es active IP Right Grant
- 2002-11-08 CA CA2465043A patent/CA2465043C/fr not_active Expired - Fee Related
- 2002-11-08 AR ARP020104298A patent/AR037285A1/es unknown
- 2002-11-08 PL PL02368456A patent/PL368456A1/xx unknown
- 2002-11-08 KR KR1020047002379A patent/KR100962325B1/ko not_active Expired - Fee Related
- 2002-11-08 US US10/491,799 patent/US7317115B2/en not_active Expired - Fee Related
2004
- 2004-05-05 NO NO20041848A patent/NO328548B1/no not_active IP Right Cessation
- 2004-05-06 ZA ZA200403454A patent/ZA200403454B/en unknown
- 2004-05-06 IL IL161866A patent/IL161866A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
EA200400656A1 (ru)	2004-10-28
PL368456A1 (en)	2005-03-21
AR037285A1 (es)	2004-11-03
HUP0402224A2 (hu)	2005-02-28
NO20041848L (no)	2004-05-05
ZA200403454B (en)	2005-08-31
IL161866A0 (en)	2005-11-20
EP1446397B1 (fr)	2005-07-06
MXPA04004365A (es)	2004-08-11
UA79248C2 (en)	2007-06-11
WO2003040122A1 (fr)	2003-05-15
DE60204982T2 (de)	2006-04-27
EP1446397A1 (fr)	2004-08-18
US20050085533A1 (en)	2005-04-21
HUP0402224A3 (en)	2007-05-29
CN1582282A (zh)	2005-02-16
AU2002349327B2 (en)	2008-10-23
DE60204982D1 (de)	2005-08-11
CA2465043C (fr)	2011-02-15
KR100962325B1 (ko)	2010-06-11
NZ531739A (en)	2005-02-25
US7317115B2 (en)	2008-01-08
ATE299138T1 (de)	2005-07-15
HRP20040395A2 (en)	2005-04-30
CA2465043A1 (fr)	2003-05-15
JP2005508988A (ja)	2005-04-07
IL161866A (en)	2010-04-29
ES2244818T3 (es)	2005-12-16
EA006980B1 (ru)	2006-06-30
BR0212770A (pt)	2004-10-13
TW200407117A (en)	2004-05-16
MY128237A (en)	2007-01-31
CN1582282B (zh)	2012-06-06
KR20050044310A (ko)	2005-05-12

Legal Events

Date	Code	Title	Description
2012-05-21	CREP	Change of representative	Representative=s name: ZACCO NORWAY AS, POSTBOKS 2003 VIKA
2013-06-24	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO317159B1 (no)	2004-08-30	Halogensubstituerte tetrasykliske tetrahydrofuranderivater
NO317156B1 (no)	2004-08-30	Substituerte tetracykliske tetrahydrofuranderivater
NO314581B1 (no)	2003-04-14	Opplösning av aminer
NO328548B1 (no)	2010-03-15	Nye mandelatsalter av substituerte tetracykliske tetrahydrofuranderivater
AU2002349327A1 (en)	2003-07-24	Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives
EP1456193B1 (fr)	2005-04-27	Preparation de derives de 3,3a,8,12b-tetrahydro-2 i h /i -dibenzo 3,4:6,7]cyclohepta 1,2-b]furane a fusion trans
EP1463722A2 (fr)	2004-10-06	PREPARATION DE DERIVES DE 3,3a,8,12b-TETRAHYDRO-2H-DIBENZO[3,4:6,7]CYCLOHEPTA[1,2-b]FURANES FUSIONNES EN CIS
NO309084B1 (no)	2000-12-11	FremgangsmÕte for fremstilling av 5-okso-3-fenyl-3- cykloheksenkarboksylsyre
HK1072938A (en)	2005-09-16	Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives
MXPA00003468A (en)	2001-12-04	Halogen substituted tetracyclic tetrahydrofuran derivatives
AU6547400A (en)	2001-04-26	Process for the preparation of piperidinylaminomethyl trifluoromethyl cyclic ether compounds
CN106928139A (zh)	2017-07-07	一种贝达喹啉杂质的合成方法
HK1029106B (en)	2003-07-18	Halogen substituted tetracyclic tetrahydrofuran derivatives