NO319953B1 - Aminoalkylsubstituerte kromanderivater, deres fremstilling og farmasoytiske sammensetninger omfattende forbindelsene, samt deres anvendelse. - Google Patents

Aminoalkylsubstituerte kromanderivater, deres fremstilling og farmasoytiske sammensetninger omfattende forbindelsene, samt deres anvendelse. Download PDF

Info

Publication number: NO319953B1
Authority: NO; Norway
Prior art keywords: formula; alk; compounds; hydrogen; compound
Prior art date: 1999-06-02

Application number

NO20015903A

Other languages

English (en)

Norwegian (no)

Other versions

NO20015903L (no

NO20015903D0 (no

Inventor

Marcel Frans Leopold De Bruyn

Kristof Van Emelen

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.)

1999-06-02

Filing date

2001-12-03

Publication date

2005-10-03

2001-12-03 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2001-12-03 Publication of NO20015903L publication Critical patent/NO20015903L/no

2001-12-03 Publication of NO20015903D0 publication Critical patent/NO20015903D0/no

2005-10-03 Publication of NO319953B1 publication Critical patent/NO319953B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 87
238000002360 preparation method Methods 0.000 title claims description 18
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
125000003016 chromanyl group Chemical class O1C(CCC2=CC=CC=C12)* 0.000 title 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
239000002585 base Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
ZVUXHPLQZACXSG-UHFFFAOYSA-N 1-[3-(3,4-dihydro-2h-chromen-2-ylmethylamino)-2-hydroxypropyl]imidazolidine-2,4-dione Chemical compound C1CC2=CC=CC=C2OC1CNCC(O)CN1CC(=O)NC1=O ZVUXHPLQZACXSG-UHFFFAOYSA-N 0.000 claims 1
125000000815 N-oxide group Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 35
-1 hydrocarbon radicals Chemical class 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
239000000543 intermediate Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 17
239000003054 catalyst Substances 0.000 description 15
230000002496 gastric effect Effects 0.000 description 15
210000002784 stomach Anatomy 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
239000000796 flavoring agent Substances 0.000 description 11
235000019634 flavors Nutrition 0.000 description 11
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
230000001771 impaired effect Effects 0.000 description 8
208000024891 symptom Diseases 0.000 description 8
238000012360 testing method Methods 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
150000001204 N-oxides Chemical class 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000003480 eluent Substances 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
238000009472 formulation Methods 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003826 tablet Substances 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
230000037406 food intake Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
230000004044 response Effects 0.000 description 5
229940076279 serotonin Drugs 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
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239000000725 suspension Substances 0.000 description 5
BSRHATGBRQMDRF-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-2-ylmethanamine Chemical class C1=CC=C2OC(CN)CCC2=C1 BSRHATGBRQMDRF-UHFFFAOYSA-N 0.000 description 4
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 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000003044 adaptive effect Effects 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000003245 coal Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
235000012631 food intake Nutrition 0.000 description 4
235000003599 food sweetener Nutrition 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000003765 sweetening agent Substances 0.000 description 4
229930192474 thiophene Natural products 0.000 description 4
239000005526 vasoconstrictor agent Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
206010059186 Early satiety Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
206010021518 Impaired gastric emptying Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 3
210000001841 basilar artery Anatomy 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
201000006549 dyspepsia Diseases 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
235000012054 meals Nutrition 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
230000003639 vasoconstrictive effect Effects 0.000 description 3
CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
206010000060 Abdominal distension Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
208000022531 anorexia Diseases 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
208000024330 bloating Diseases 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
NNOYLBKZPCUCQT-UHFFFAOYSA-L calcium;1,1-dioxo-1,2-benzothiazol-3-olate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Ca+2].C1=CC=C2C([O-])=NS(=O)(=O)C2=C1.C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 NNOYLBKZPCUCQT-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000002490 cerebral effect Effects 0.000 description 2
230000008859 change Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000006264 debenzylation reaction Methods 0.000 description 2
206010061428 decreased appetite Diseases 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
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238000004128 high performance liquid chromatography Methods 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000010255 intramuscular injection Methods 0.000 description 2
239000007927 intramuscular injection Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
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229920003303 ion-exchange polymer Polymers 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
NJVDPMFWASDKDP-UHFFFAOYSA-N n,n-dibenzyl-1-(oxiran-2-yl)methanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1CO1 NJVDPMFWASDKDP-UHFFFAOYSA-N 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
235000013615 non-nutritive sweetener Nutrition 0.000 description 2
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239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
JADFCQKRKICRKI-UHFFFAOYSA-N quinoline;sulfane Chemical compound S.N1=CC=CC2=CC=CC=C21 JADFCQKRKICRKI-UHFFFAOYSA-N 0.000 description 2
238000005932 reductive alkylation reaction Methods 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000012453 solvate Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
235000019408 sucralose Nutrition 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
230000036977 tonic contraction Effects 0.000 description 2
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AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
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NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 1
SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 description 1
HDNFRIGUENGYSY-UHFFFAOYSA-N 1-[3-(dibenzylamino)-2-hydroxypropyl]pyrimidin-2-one Chemical compound C1=CC=NC(=O)N1CC(O)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 HDNFRIGUENGYSY-UHFFFAOYSA-N 0.000 description 1
ZZKASKLMZQUERL-UHFFFAOYSA-N 1-[3-[benzyl(3,4-dihydro-2h-chromen-2-ylmethyl)amino]-2-hydroxypropyl]imidazolidine-2,4-dione Chemical compound C1C(=O)NC(=O)N1CC(O)CN(CC1OC2=CC=CC=C2CC1)CC1=CC=CC=C1 ZZKASKLMZQUERL-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ZQFGTJLFYMYOQE-UHFFFAOYSA-N 2-methyl-3,4-dihydrochromen-2-amine Chemical class C1=CC=C2OC(C)(N)CCC2=C1 ZQFGTJLFYMYOQE-UHFFFAOYSA-N 0.000 description 1
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-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
GLXZQISZDFGOTI-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-3-yl)-3-(2-hydroxyethyl)-1-piperidin-1-ylimidazolidin-2-one Chemical class O1C(COC2=C1C=CC=C2)C2N(C(N(C2)N2CCCCC2)=O)CCO GLXZQISZDFGOTI-UHFFFAOYSA-N 0.000 description 1
KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Child & Adolescent Psychology (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyrane Compounds (AREA)

NO20015903A 1999-06-02 2001-12-03 Aminoalkylsubstituerte kromanderivater, deres fremstilling og farmasoytiske sammensetninger omfattende forbindelsene, samt deres anvendelse. NO319953B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99201747		1999-06-02
PCT/EP2000/004746 WO2000075136A1 (en)	1999-06-02	2000-05-23	Aminoalkyl substituted (benzodioxan, benzofuran or benzopyran) derivatives

Publications (3)

Publication Number	Publication Date
NO20015903L NO20015903L (no)	2001-12-03
NO20015903D0 NO20015903D0 (no)	2001-12-03
NO319953B1 true NO319953B1 (no)	2005-10-03

Family

ID=8240260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20015903A NO319953B1 (no)	1999-06-02	2001-12-03	Aminoalkylsubstituerte kromanderivater, deres fremstilling og farmasoytiske sammensetninger omfattende forbindelsene, samt deres anvendelse.

Country Status (33)

Country	Link
US (2)	US6864273B1 (de)
EP (1)	EP1187829B1 (de)
JP (1)	JP2003501427A (de)
KR (1)	KR100699512B1 (de)
CN (1)	CN1150191C (de)
AR (1)	AR033334A1 (de)
AT (1)	ATE256125T1 (de)
AU (1)	AU773773B2 (de)
BG (1)	BG65269B1 (de)
BR (1)	BR0011237A (de)
CA (1)	CA2374902C (de)
CZ (1)	CZ20014177A3 (de)
DE (1)	DE60007124T2 (de)
DK (1)	DK1187829T3 (de)
EA (1)	EA004645B1 (de)
EE (1)	EE04780B1 (de)
ES (1)	ES2212774T3 (de)
HR (1)	HRP20010868A2 (de)
HU (1)	HUP0201404A3 (de)
IL (2)	IL146840A0 (de)
MX (1)	MXPA01012330A (de)
MY (1)	MY120618A (de)
NO (1)	NO319953B1 (de)
NZ (1)	NZ514993A (de)
PL (1)	PL198552B1 (de)
PT (1)	PT1187829E (de)
SI (1)	SI1187829T1 (de)
SK (1)	SK285619B6 (de)
TR (1)	TR200103430T2 (de)
TW (1)	TWI289559B (de)
UA (1)	UA73122C2 (de)
WO (1)	WO2000075136A1 (de)
ZA (1)	ZA200109860B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2003501428A (ja)	1999-06-02	2003-01-14	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	ピロリジニル、ピペリジニルもしくはホモピペリジニル置換（ベンゾジオキサン、ベンゾフランもしくはベンゾピラン）誘導体
JO2352B1 (en) *	2000-06-22	2006-12-12	جانسين فارماسيوتيكا ان. في	Compounds for the treatment of non-adaptation of the bottom of the uterus
JO2654B1 (en)	2000-09-04	2012-06-17	شركة جانسين فارماسوتيكا ان. في	Multiple aryl caroxa amides are useful as lipid - lowering agents
JO2409B1 (en)	2000-11-21	2007-06-17	شركة جانسين فارماسوتيكا ان. في	Second-phenyl carboxy amides are useful as lipid-lowering agents
US20050176788A1 (en) *	2002-04-08	2005-08-11	Zeria Pharmaceutical Co., Ltd.	Therapeutic agent for food competence disorder in stomach
CN101120002A (zh)	2005-02-17	2008-02-06	惠氏公司	环烷基稠合的吲哚、苯并噻吩、苯并呋喃和茚衍生物
GEP201706656B (en)	2011-11-11	2017-04-25	Pfizer	2-thiopyrimidinones
MA42035A (fr)	2015-05-05	2018-03-14	Pfizer	2-thiopyrimidinones

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US3910930A (en) *	1973-01-04	1975-10-07	Janssen Pharmaceutica Nv	1-{55 1-{8 2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl{9 -4-piperidyl{56 -2-benzimidazolinones
US3929801A (en)	1973-11-20	1975-12-30	Janssen Pharmaceutica Nv	2-Benzimidazolinones
GR71865B (de)	1978-03-20	1983-07-07	Ciba Geigy
DE2852945A1 (de)	1978-12-07	1980-06-26	Boehringer Sohn Ingelheim	Benzodioxanyl-hydroxyaethylpiperidyl- imidazolidinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US4329348A (en)	1979-02-26	1982-05-11	Ciba-Geigy Corporation	N-Oxacyclic-alkylpiperidines as psychostimulants
DE3124366A1 (de)	1981-06-20	1982-12-30	Hoechst Ag, 6000 Frankfurt	N-oxacyclyl-alkylpiperidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische praeparate und deren verwendung
FR2533584B1 (fr)	1982-09-28	1986-03-21	Pasteur Institut	Procede de detection du pouvoir mutagene de substances, susceptibles d'induire la deterioration d'adn cellulaires, mettant en jeu la production d'une reponse sos
DE3901814A1 (de)	1988-07-28	1990-02-01	Bayer Ag	Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga
DE4140540A1 (de)	1991-12-09	1993-06-17	Bayer Ag	Neue azaheterocyclylmethyl-chromane
SI9300097B (en)	1992-02-27	2001-12-31	Janssen Pharmaceutica Nv	(benzodioxan, benzofuran or benzopyran) alkylamino) alkyl substituted guanidines
DE4319038A1 (de) *	1993-06-08	1994-12-15	Bayer Ag	Verwendung von teilweise bekannten substituierten Chromanen als Arzneimittel, neue Wirkstoffe und Verfahren zu ihrer Herstellung
DE69433401T2 (de)	1993-08-19	2004-09-16	Janssen Pharmaceutica N.V.	Gefässverengende dihydrobenzopyranderivate
US5541199A (en)	1995-06-02	1996-07-30	American Home Products Corporation	Chroman-2-ylmethylamino derivatives
FR2744451B1 (fr)	1996-02-01	1998-04-24	Pf Medicament	Nouvelles imidazolidinones, pyrimidinones, et 1,3-diazepin-2 -ones, leur preparation et leurs applications en therapeutique
US6133277A (en) *	1997-12-05	2000-10-17	Janssen Pharmaceutica N.V.	(Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties
JP2003501428A (ja)	1999-06-02	2003-01-14	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	ピロリジニル、ピペリジニルもしくはホモピペリジニル置換（ベンゾジオキサン、ベンゾフランもしくはベンゾピラン）誘導体
JO2352B1 (en)	2000-06-22	2006-12-12	جانسين فارماسيوتيكا ان. في	Compounds for the treatment of non-adaptation of the bottom of the uterus

2000
- 2000-05-23 AT AT00940267T patent/ATE256125T1/de not_active IP Right Cessation
- 2000-05-23 BR BR0011237-2A patent/BR0011237A/pt not_active Application Discontinuation
- 2000-05-23 JP JP2001502419A patent/JP2003501427A/ja not_active Withdrawn
- 2000-05-23 AU AU55256/00A patent/AU773773B2/en not_active Ceased
- 2000-05-23 DK DK00940267T patent/DK1187829T3/da active
- 2000-05-23 MX MXPA01012330A patent/MXPA01012330A/es unknown
- 2000-05-23 US US09/980,452 patent/US6864273B1/en not_active Expired - Lifetime
- 2000-05-23 HR HR20010868A patent/HRP20010868A2/hr not_active Application Discontinuation
- 2000-05-23 ES ES00940267T patent/ES2212774T3/es not_active Expired - Lifetime
- 2000-05-23 IL IL14684000A patent/IL146840A0/xx active IP Right Grant
- 2000-05-23 PL PL352112A patent/PL198552B1/pl not_active IP Right Cessation
- 2000-05-23 KR KR1020017013659A patent/KR100699512B1/ko not_active Expired - Fee Related
- 2000-05-23 EE EEP200100639A patent/EE04780B1/xx not_active IP Right Cessation
- 2000-05-23 CA CA002374902A patent/CA2374902C/en not_active Expired - Lifetime
- 2000-05-23 PT PT00940267T patent/PT1187829E/pt unknown
- 2000-05-23 UA UA2001128825A patent/UA73122C2/uk unknown
- 2000-05-23 TR TR2001/03430T patent/TR200103430T2/xx unknown
- 2000-05-23 EA EA200101236A patent/EA004645B1/ru not_active IP Right Cessation
- 2000-05-23 EP EP00940267A patent/EP1187829B1/de not_active Expired - Lifetime
- 2000-05-23 CZ CZ20014177A patent/CZ20014177A3/cs unknown
- 2000-05-23 SI SI200030293T patent/SI1187829T1/xx unknown
- 2000-05-23 CN CNB008083185A patent/CN1150191C/zh not_active Expired - Fee Related
- 2000-05-23 WO PCT/EP2000/004746 patent/WO2000075136A1/en not_active Ceased
- 2000-05-23 SK SK1703-2001A patent/SK285619B6/sk not_active IP Right Cessation
- 2000-05-23 HU HU0201404A patent/HUP0201404A3/hu unknown
- 2000-05-23 NZ NZ514993A patent/NZ514993A/en unknown
- 2000-05-23 DE DE60007124T patent/DE60007124T2/de not_active Expired - Lifetime
- 2000-05-24 TW TW089109971A patent/TWI289559B/zh not_active IP Right Cessation
- 2000-05-30 MY MYPI20002411A patent/MY120618A/en unknown
- 2000-06-01 AR ARP000102714A patent/AR033334A1/es unknown
2001
- 2001-11-28 BG BG106156A patent/BG65269B1/bg unknown
- 2001-11-29 IL IL146840A patent/IL146840A/en not_active IP Right Cessation
- 2001-11-29 ZA ZA200109860A patent/ZA200109860B/xx unknown
- 2001-12-03 NO NO20015903A patent/NO319953B1/no not_active IP Right Cessation
2004
- 2004-11-29 US US10/999,187 patent/US7273862B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BG106156A (en)	2002-05-31
CA2374902A1 (en)	2000-12-14
US20050096378A1 (en)	2005-05-05
IL146840A0 (en)	2002-07-25
UA73122C2 (en)	2005-06-15
EA200101236A1 (ru)	2002-08-29
CN1150191C (zh)	2004-05-19
DE60007124D1 (de)	2004-01-22
JP2003501427A (ja)	2003-01-14
MXPA01012330A (es)	2002-07-30
AR033334A1 (es)	2003-12-17
EE04780B1 (et)	2007-02-15
NO20015903L (no)	2001-12-03
CZ20014177A3 (cs)	2002-05-15
CA2374902C (en)	2009-09-15
EE200100639A (et)	2003-02-17
ES2212774T3 (es)	2004-08-01
TR200103430T2 (tr)	2002-06-21
BG65269B1 (bg)	2007-11-30
SI1187829T1 (en)	2004-04-30
PT1187829E (pt)	2004-04-30
SK17032001A3 (sk)	2002-07-02
EP1187829A1 (de)	2002-03-20
US6864273B1 (en)	2005-03-08
AU5525600A (en)	2000-12-28
SK285619B6 (sk)	2007-05-03
KR100699512B1 (ko)	2007-03-26
DE60007124T2 (de)	2004-09-23
MY120618A (en)	2005-11-30
EP1187829B1 (de)	2003-12-10
US7273862B2 (en)	2007-09-25
PL352112A1 (en)	2003-07-28
IL146840A (en)	2006-12-10
NZ514993A (en)	2003-05-30
HUP0201404A3 (en)	2005-02-28
BR0011237A (pt)	2002-03-05
EA004645B1 (ru)	2004-06-24
TWI289559B (en)	2007-11-11
AU773773B2 (en)	2004-06-03
NO20015903D0 (no)	2001-12-03
CN1353707A (zh)	2002-06-12
PL198552B1 (pl)	2008-06-30
HRP20010868A2 (en)	2003-04-30
ZA200109860B (en)	2003-05-28
DK1187829T3 (da)	2004-04-13
HUP0201404A2 (en)	2002-08-28
WO2000075136A1 (en)	2000-12-14
KR20010110806A (ko)	2001-12-13
ATE256125T1 (de)	2003-12-15

Legal Events

Date	Code	Title	Description
2010-12-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US6747045B2 (en)	2004-06-08	(Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties
EP1187829B1 (de)	2003-12-10	Aminoalkyl substituierte (benzodioxane,benzofurane oder benzopyrane) derivate
NO319950B1 (no)	2005-10-03	Pyrrolidinyl- eller piperidinyl-substituerte kromanderivater, deres fremstilling og farmasoytiske sammensetninger omfattende disse samt deres anvendelse.
MXPA00005524A (en)	2002-05-09	(benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties
HK1028400B (en)	2006-11-10	(benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties