UA79248C2 - Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives - Google Patents

Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives Download PDF

Info

Publication number: UA79248C2
Authority: UA; Ukraine
Prior art keywords: mandelic acid; acid salt; formula; tetrahydro; cyclohepta
Prior art date: 2001-11-09

Application number

UA20040604168A

Other languages

English (en)

Ukrainian (uk)

Inventor

Bart Petrus Anna Maria Medaer

Sigrid Carl Maria Stokbroekx

Yves Georges Ruysschaert

Joannes Josephus Maria Willems

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

2002-08-11

Publication date

2007-06-11

2002-08-11 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2007-06-11 Publication of UA79248C2 publication Critical patent/UA79248C2/uk

Links

WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title abstract description 13
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical class [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 title abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 60
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 51
239000000203 mixture Substances 0.000 claims description 25
239000002904 solvent Substances 0.000 claims description 23
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
208000028017 Psychotic disease Diseases 0.000 claims description 5
206010013663 drug dependence Diseases 0.000 claims description 5
208000011117 substance-related disease Diseases 0.000 claims description 5
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
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical class OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 4
229960002510 mandelic acid Drugs 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
239000004480 active ingredient Substances 0.000 claims description 3
150000004820 halides Chemical class 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
239000000460 chlorine Substances 0.000 claims description 2
239000002178 crystalline material Substances 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
229940126601 medicinal product Drugs 0.000 claims 2
238000000746 purification Methods 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 20
-1 for example Chemical group 0.000 abstract description 15
239000003814 drug Substances 0.000 abstract description 8
208000015114 central nervous system disease Diseases 0.000 abstract description 4
230000002265 prevention Effects 0.000 abstract description 4
208000024172 Cardiovascular disease Diseases 0.000 abstract description 3
208000018522 Gastrointestinal disease Diseases 0.000 abstract description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
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 abstract description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000000815 N-oxide group Chemical group 0.000 abstract 1
239000012736 aqueous medium Substances 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 36
238000000034 method Methods 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 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 14
239000000126 substance Substances 0.000 description 13
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
229940095064 tartrate Drugs 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
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238000006243 chemical reaction Methods 0.000 description 6
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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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
239000007924 injection Substances 0.000 description 5
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 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
239000007788 liquid Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000012044 organic layer 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
238000002336 sorption--desorption measurement Methods 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
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
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
238000005804 alkylation reaction Methods 0.000 description 3
125000004429 atom Chemical group 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
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229940125773 compound 10 Drugs 0.000 description 3
238000003795 desorption Methods 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
239000012535 impurity Substances 0.000 description 3
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000002245 particle Substances 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
150000003892 tartrate salts Chemical class 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
229920003169 water-soluble polymer Polymers 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-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
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-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
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 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
230000002378 acidificating effect Effects 0.000 description 2
230000009471 action Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
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239000002585 base Substances 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
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229940125898 compound 5 Drugs 0.000 description 2
229940097362 cyclodextrins Drugs 0.000 description 2
WWBGONGKRSWMGE-UHFFFAOYSA-N cycloheptene Chemical compound [CH]1CCCC=CC1 WWBGONGKRSWMGE-UHFFFAOYSA-N 0.000 description 2
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238000000227 grinding Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 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
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150000002978 peroxides Chemical class 0.000 description 2
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XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
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GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
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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)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Addiction (AREA)
Anesthesiology (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)

UA20040604168A 2001-11-09 2002-08-11 Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives UA79248C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01204465		2001-11-09
PCT/EP2002/011136 WO2003040122A1 (en)	2001-11-09	2002-11-08	Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives

Publications (1)

Publication Number	Publication Date
UA79248C2 true UA79248C2 (en)	2007-06-11

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ID=8181272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20040604168A UA79248C2 (en)	2001-11-09	2002-08-11	Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives

Country Status (25)

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

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Publication number	Priority date	Publication date	Assignee	Title
ATE294168T1 (de) *	2001-12-07	2005-05-15	Janssen Pharmaceutica Nv	Herstellung von trans-kondensierte 3,3a,8,12b- tetrahydro-2h-dibenzo(3,4:6,7)cyclohepta(1,2- b)furan derivaten
WO2005013969A1 (en) *	2003-07-15	2005-02-17	Janssen Pharmaceutica N.V.	Antipsychotic agent with socializing properties
EP1824820A2 (de)	2004-12-07	2007-08-29	Janssen Pharmaceutica N.V.	Substituierte derivate von tetracyclischem tetrahydrofuran, pyrrolidin und tetrahydrothiopen
NZ556272A (en)	2005-01-27	2009-12-24	Janssen Pharmaceutica Nv	Heterocyclic tetracyclic tetrahydrofuran derivatives as 5HT2 inhibitors in the treatment of CNS disorders
MX2007016247A (es)	2005-06-17	2008-03-10	Janssen Pharmaceutica Nv	Derivados de tetrahidrofurano tetraciclicos novedosos que contienen una cadena lateral de amida ciclica.
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

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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
ES2158094T3 (es) *	1994-03-16	2001-09-01	Cenes Ltd	Sales de adicion de acido de compuestos de 2,3,4,5-tetrahidro-1h-3-benzazepina.
BR9706639A (pt) *	1996-04-12	1999-01-12	Janssen Pharmaceutica Nv	Derivados de tetrahidrofurano tetracíclicos substituídos
CA2240161C (en)	1996-05-20	2005-05-24	Janssen Pharmaceutica N.V.	Antifungal compositions with improved bioavailability
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 (de) *	2000-09-06	2003-12-10	Pfizer Products Inc.	Ein Neutrophilhemmender Faktor und ein selektive NMDA-NR2B Rezeptor Antagonisten enthaltende Kombinationspräparate zur Behandlung von Schlaganfällen und traumatischen Gehirnschäden

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

Also Published As

Publication number	Publication date
DE60204982D1 (de)	2005-08-11
CN1582282A (zh)	2005-02-16
ZA200403454B (en)	2005-08-31
EA200400656A1 (ru)	2004-10-28
BR0212770A (pt)	2004-10-13
IL161866A0 (en)	2005-11-20
US7317115B2 (en)	2008-01-08
TW200407117A (en)	2004-05-16
IL161866A (en)	2010-04-29
MXPA04004365A (es)	2004-08-11
ES2244818T3 (es)	2005-12-16
MY128237A (en)	2007-01-31
JP2005508988A (ja)	2005-04-07
EA006980B1 (ru)	2006-06-30
EP1446397B1 (de)	2005-07-06
PL368456A1 (en)	2005-03-21
AU2002349327B2 (en)	2008-10-23
CN1582282B (zh)	2012-06-06
KR20050044310A (ko)	2005-05-12
HRP20040395A2 (en)	2005-04-30
HUP0402224A2 (hu)	2005-02-28
HUP0402224A3 (en)	2007-05-29
WO2003040122A1 (en)	2003-05-15
ATE299138T1 (de)	2005-07-15
NZ531739A (en)	2005-02-25
AR037285A1 (es)	2004-11-03
KR100962325B1 (ko)	2010-06-11
CA2465043A1 (en)	2003-05-15
US20050085533A1 (en)	2005-04-21
CA2465043C (en)	2011-02-15
DE60204982T2 (de)	2006-04-27
NO328548B1 (no)	2010-03-15
NO20041848L (no)	2004-05-05
EP1446397A1 (de)	2004-08-18

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