UA74576C2 - Compounds of dioxinepyridines, a method for producing thereof (variants), a pharmaceutical composition based thereon and a method for producing thereof - Google Patents

Compounds of dioxinepyridines, a method for producing thereof (variants), a pharmaceutical composition based thereon and a method for producing thereof Download PDF

Info

Publication number: UA74576C2
Authority: UA; Ukraine
Prior art keywords: formula; alkyl; group; сно; mol
Prior art date: 2000-06-22

Application number

UA20021210045A

Other languages

English (en)

Ukrainian (uk)

Inventor

Brauyn Marcel Frans Leopold De

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.)

2000-06-22

Filing date

2001-06-13

Publication date

2006-01-16

2001-06-13 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2006-01-16 Publication of UA74576C2 publication Critical patent/UA74576C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 195
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title description 3
-1 C3-6cycloaalcyl Chemical group 0.000 claims abstract description 46
239000001257 hydrogen Substances 0.000 claims abstract description 44
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
150000003839 salts Chemical class 0.000 claims abstract description 29
238000000034 method Methods 0.000 claims abstract description 27
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 25
239000002253 acid Substances 0.000 claims abstract description 19
150000002431 hydrogen Chemical class 0.000 claims abstract description 17
229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
239000001301 oxygen Substances 0.000 claims abstract description 16
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
239000011593 sulfur Chemical group 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
239000003814 drug Substances 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims description 116
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 12
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 11
239000002585 base Substances 0.000 claims description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
235000013305 food Nutrition 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
239000003513 alkali Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
230000007935 neutral effect Effects 0.000 claims description 4
238000005932 reductive alkylation reaction Methods 0.000 claims description 4
125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
230000009466 transformation Effects 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000004951 trihalomethoxy group Chemical group 0.000 claims description 2
125000004953 trihalomethyl group Chemical group 0.000 claims description 2
239000012458 free base Substances 0.000 claims 3
101150071927 AANAT gene Proteins 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 144
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 20
238000009472 formulation Methods 0.000 abstract description 8
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 1
125000000815 N-oxide group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 122
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 110
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
239000011541 reaction mixture Substances 0.000 description 67
239000000243 solution Substances 0.000 description 58
150000003254 radicals Chemical class 0.000 description 51
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
239000012044 organic layer Substances 0.000 description 42
239000000741 silica gel Substances 0.000 description 39
229910002027 silica gel Inorganic materials 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
210000002784 stomach Anatomy 0.000 description 32
238000002844 melting Methods 0.000 description 31
230000008018 melting Effects 0.000 description 31
235000019441 ethanol Nutrition 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000003054 catalyst Substances 0.000 description 21
239000000706 filtrate Substances 0.000 description 21
238000001816 cooling Methods 0.000 description 20
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238000004440 column chromatography Methods 0.000 description 18
230000002496 gastric effect Effects 0.000 description 17
238000004587 chromatography analysis Methods 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 14
230000002441 reversible effect Effects 0.000 description 14
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000012047 saturated solution Substances 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
239000012359 Methanesulfonyl chloride Substances 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000003480 eluent Substances 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 9
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
208000024891 symptom Diseases 0.000 description 8
238000012360 testing method Methods 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000005457 ice water Substances 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
239000000654 additive Substances 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
210000002599 gastric fundus Anatomy 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000005526 vasoconstrictor agent Substances 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
230000001771 impaired effect Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000003044 adaptive effect Effects 0.000 description 3
210000001841 basilar artery Anatomy 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000292 calcium oxide Substances 0.000 description 3
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
230000008602 contraction Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
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238000002474 experimental method Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
230000004044 response Effects 0.000 description 3
230000036186 satiety Effects 0.000 description 3
235000019627 satiety Nutrition 0.000 description 3
229940076279 serotonin Drugs 0.000 description 3
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239000000375 suspending agent Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
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 2
CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
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UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
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HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 1
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BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
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229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
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
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
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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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

UA20021210045A 2000-06-22 2001-06-13 Compounds of dioxinepyridines, a method for producing thereof (variants), a pharmaceutical composition based thereon and a method for producing thereof UA74576C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00202180		2000-06-22
PCT/EP2001/006749 WO2001098306A1 (en)	2000-06-22	2001-06-13	Compounds for treating impaired fundic relaxation

Publications (1)

Publication Number	Publication Date
UA74576C2 true UA74576C2 (en)	2006-01-16

Family

ID=8171674

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20021210045A UA74576C2 (en)	2000-06-22	2001-06-13	Compounds of dioxinepyridines, a method for producing thereof (variants), a pharmaceutical composition based thereon and a method for producing thereof

Country Status (33)

Country	Link
US (2)	US7081453B2 (is)
EP (1)	EP1296987B1 (is)
JP (1)	JP4911860B2 (is)
KR (1)	KR100821107B1 (is)
CN (2)	CN100516066C (is)
AR (1)	AR032158A1 (is)
AT (1)	ATE312104T1 (is)
AU (1)	AU783292B2 (is)
BG (1)	BG65895B1 (is)
BR (1)	BR0111859B1 (is)
CA (1)	CA2410233C (is)
CZ (1)	CZ305005B6 (is)
DE (1)	DE60115647T2 (is)
EA (1)	EA005760B1 (is)
EE (1)	EE04878B1 (is)
EG (1)	EG24462A (is)
ES (1)	ES2254467T3 (is)
HR (1)	HRP20020988B1 (is)
HU (1)	HU227398B1 (is)
IL (2)	IL153559A0 (is)
IS (1)	IS2618B (is)
JO (1)	JO2352B1 (is)
MX (1)	MXPA02012844A (is)
MY (1)	MY155267A (is)
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NZ (1)	NZ522519A (is)
PA (1)	PA8519601A1 (is)
PL (1)	PL201656B1 (is)
SA (1)	SA01220442B1 (is)
SK (1)	SK287730B6 (is)
UA (1)	UA74576C2 (is)
WO (1)	WO2001098306A1 (is)
ZA (1)	ZA200210303B (is)

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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
AU2004233863B2 (en)	2003-04-24	2010-06-17	Incyte Holdings Corporation	Aza spiro alkane derivatives as inhibitors of metalloproteases
JP4896476B2 (ja) *	2005-09-16	2012-03-14	広栄化学工業株式会社	メチルオキシメチルアミノピリジン誘導体及びその製造方法
US7999107B2 (en)	2007-01-31	2011-08-16	Merck Sharp & Dohme Corp.	Substituted pyrano[2,3-B]pyridine derivatives as cannabinoid-1 receptor modulators
CA2685860A1 (en) *	2007-05-10	2008-11-20	Amr Technology, Inc.	Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
GEP201706656B (en)	2011-11-11	2017-04-25	Pfizer	2-thiopyrimidinones
MA42035A (fr)	2015-05-05	2018-03-14	Pfizer	2-thiopyrimidinones
CN105481839B (zh) *	2015-11-23	2018-05-11	安徽千和新材料科技发展有限公司	一种光活性环氧啉对映体的制备方法
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2001
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2002
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Also Published As

Publication number	Publication date
HRP20020988B1 (en)	2011-06-30
HU227398B1 (hu)	2011-05-30
ATE312104T1 (de)	2005-12-15
EE200200694A (et)	2004-06-15
JP2004501157A (ja)	2004-01-15
HK1057896A1 (en)	2004-04-23
CA2410233A1 (en)	2001-12-27
IL153559A (en)	2008-03-20
CN100516066C (zh)	2009-07-22
KR20030007566A (ko)	2003-01-23
HRP20020988A2 (en)	2005-02-28
CN1288157C (zh)	2006-12-06
US7081453B2 (en)	2006-07-25
EG24462A (en)	2009-07-16
JO2352B1 (en)	2006-12-12
BG65895B1 (bg)	2010-04-30
SA01220442B1 (ar)	2008-05-21
AR032158A1 (es)	2003-10-29
ES2254467T3 (es)	2006-06-16
HUP0301185A3 (en)	2009-03-30
EA005760B1 (ru)	2005-06-30
MXPA02012844A (es)	2003-05-15
WO2001098306A1 (en)	2001-12-27
BR0111859A (pt)	2003-05-13
DE60115647T2 (de)	2006-08-24
ZA200210303B (en)	2004-03-19
CN1437602A (zh)	2003-08-20
CA2410233C (en)	2011-01-25
US7423048B2 (en)	2008-09-09
US20040019051A1 (en)	2004-01-29
NO20026219L (no)	2003-02-17
AU783292B2 (en)	2005-10-13
PL358886A1 (en)	2004-08-23
BG107313A (bg)	2003-06-30
NO20026219D0 (no)	2002-12-23
HUP0301185A2 (hu)	2003-08-28
NZ522519A (en)	2003-09-26
BR0111859B1 (pt)	2015-01-06
CZ305005B6 (cs)	2015-03-25
IL153559A0 (en)	2003-07-06
KR100821107B1 (ko)	2008-04-14
AU8386401A (en)	2002-01-02
CZ2003115A3 (cs)	2003-06-18
PA8519601A1 (es)	2002-08-26
DE60115647D1 (de)	2006-01-12
EP1296987A1 (en)	2003-04-02
IS2618B (is)	2010-04-15
SK492003A3 (en)	2003-07-01
EE04878B1 (et)	2007-08-15
EP1296987B1 (en)	2005-12-07
NO328547B1 (no)	2010-03-15
IS6591A (is)	2002-10-25
US20060142318A1 (en)	2006-06-29
EA200300049A1 (ru)	2003-04-24
PL201656B1 (pl)	2009-04-30
JP4911860B2 (ja)	2012-04-04
CN1781921A (zh)	2006-06-07
SK287730B6 (en)	2011-07-06
MY155267A (en)	2015-09-30

Publication	Publication Date	Title
JP4530530B2 (ja)	2010-08-25	胃運動性の３−もしくは４−置換４−（アミノメチル）−ピペリジン誘導体の単環式ベンズアミド
HRP20000340A2 (en)	2001-04-30	(benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties
JP4911860B2 (ja)	2012-04-04	障害のある底部弛緩を処置するための組成物
ES2231189T3 (es)	2005-05-16	Derivados de benzodioxano o benzopirano sustituidos con pirrolidinilo, piperidinilo u homopiperidinilo.
UA73122C2 (en)	2005-06-15	Derivatives of benzodioxane, benzofuran or benzopyran substituted by aminoalkyl
DE602004009069T2 (de)	2008-06-19	4-(aminomethyl)-piperidinbenzamide als 5ht4-antagonisten
MXPA00005524A (en)	2002-05-09	(benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties