BG63545B1 - N-[4-(хетероарилметил)фенил]-хетероариламини - Google Patents

N-[4-(хетероарилметил)фенил]-хетероариламини Download PDF

Info

Publication number: BG63545B1
Authority: BG; Bulgaria
Prior art keywords: alkyl; formula; aryl; amino; compound
Prior art date: 1996-06-27

Application number

BG103013A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG103013A (en

Inventor

Marc Venet

Dominique Mabire

Jean Lacrampe

Gerard Sanz

Original Assignee

Janssen Pharmaceutica N.V.

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.)

1996-06-27

Filing date

1998-12-14

Publication date

2002-04-30

1998-12-14 Application filed by Janssen Pharmaceutica N.V. filed Critical Janssen Pharmaceutica N.V.

1999-09-30 Publication of BG103013A publication Critical patent/BG103013A/xx

2002-04-30 Publication of BG63545B1 publication Critical patent/BG63545B1/bg

Links

125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 38
-1 trazolyl Chemical group 0.000 claims abstract description 141
150000001875 compounds Chemical class 0.000 claims abstract description 136
125000003118 aryl group Chemical group 0.000 claims abstract description 54
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
239000001257 hydrogen Substances 0.000 claims abstract description 40
150000003839 salts Chemical class 0.000 claims abstract description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 14
125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 9
125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 9
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 115
239000002904 solvent Substances 0.000 claims description 78
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
238000006243 chemical reaction Methods 0.000 claims description 29
239000008194 pharmaceutical composition Substances 0.000 claims description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
239000002585 base Substances 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
239000012442 inert solvent Substances 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 15
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 10
239000003153 chemical reaction reagent Substances 0.000 claims description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 7
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000001425 triazolyl group Chemical group 0.000 claims description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000002757 morpholinyl group Chemical group 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
230000009466 transformation Effects 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
229910021645 metal ion Inorganic materials 0.000 claims description 2
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 14
125000001475 halogen functional group Chemical group 0.000 claims 7
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000005110 aryl thio group Chemical group 0.000 claims 1
125000005604 azodicarboxylate group Chemical group 0.000 claims 1
229910052796 boron Inorganic materials 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
239000002002 slurry Substances 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 129
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 20
150000001204 N-oxides Chemical class 0.000 abstract description 7
239000000543 intermediate Substances 0.000 description 113
239000000243 solution Substances 0.000 description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
239000012044 organic layer Substances 0.000 description 33
239000002244 precipitate Substances 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
235000019439 ethyl acetate Nutrition 0.000 description 27
239000003480 eluent Substances 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
201000010099 disease Diseases 0.000 description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 14
229960005084 calcitriol Drugs 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 14
229930002330 retinoic acid Natural products 0.000 description 14
GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 13
239000011612 calcitriol Substances 0.000 description 13
235000020964 calcitriol Nutrition 0.000 description 13
150000003254 radicals Chemical class 0.000 description 13
229960001727 tretinoin Drugs 0.000 description 13
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
235000011114 ammonium hydroxide Nutrition 0.000 description 11
108010037444 diisopropylglutathione ester Proteins 0.000 description 11
230000000694 effects Effects 0.000 description 11
150000002431 hydrogen Chemical class 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
239000008213 purified water Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
239000003826 tablet Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003814 drug Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000011282 treatment Methods 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
239000002552 dosage form Substances 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
235000015320 potassium carbonate Nutrition 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
230000004060 metabolic process Effects 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011734 sodium Chemical class 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
201000004681 Psoriasis Diseases 0.000 description 5
230000002159 abnormal effect Effects 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
239000002202 Polyethylene glycol Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000000470 constituent Substances 0.000 description 4
239000006071 cream Substances 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
230000004069 differentiation Effects 0.000 description 4
229940079593 drug Drugs 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
238000004811 liquid chromatography Methods 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
238000011200 topical administration Methods 0.000 description 4
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
241000282414 Homo sapiens Species 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
230000009471 action Effects 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
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 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000002537 cosmetic Substances 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
230000002124 endocrine Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229960001031 glucose Drugs 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000006210 lotion Substances 0.000 description 3
239000011777 magnesium Chemical class 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000006187 pill Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
208000002874 Acne Vulgaris Diseases 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
206010008570 Chloasma Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
230000005526 G1 to G0 transition Effects 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
208000003351 Melanosis Diseases 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
241000700159 Rattus Species 0.000 description 2
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125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002304 perfume Substances 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
TWHXWYVOWJCXSI-UHFFFAOYSA-N phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O TWHXWYVOWJCXSI-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
206010035116 pityriasis rubra pilaris Diseases 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000004492 retinoid derivatives Chemical class 0.000 description 1
238000012552 review Methods 0.000 description 1
201000004700 rosacea Diseases 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000565 sealant Substances 0.000 description 1
230000021148 sequestering of metal ion Effects 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
201000000849 skin cancer Diseases 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
229940075554 sorbate Drugs 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000037072 sun protection Effects 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-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
229940100611 topical cream Drugs 0.000 description 1
229940042129 topical gel Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-M undecanoate Chemical compound CCCCCCCCCCC([O-])=O ZDPHROOEEOARMN-UHFFFAOYSA-M 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- C07D417/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG103013A 1996-06-27 1998-12-14 N-[4-(хетероарилметил)фенил]-хетероариламини BG63545B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP96201781		1996-06-27
PCT/EP1997/003248 WO1997049704A1 (en)	1996-06-27	1997-06-19	N-[4-(heteroarylmethyl)phenyl]-heteroarylamines

Publications (2)

Publication Number	Publication Date
BG103013A BG103013A (en)	1999-09-30
BG63545B1 true BG63545B1 (bg)	2002-04-30

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ID=8224119

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Application Number	Title	Priority Date	Filing Date
BG103013A BG63545B1 (bg)	1996-06-27	1998-12-14	N-[4-(хетероарилметил)фенил]-хетероариламини

Country Status (32)

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US (5)	US6124330A (uk)
EP (1)	EP0907650B1 (uk)
JP (1)	JP3404749B2 (uk)
KR (1)	KR100365312B1 (uk)
CN (1)	CN1102593C (uk)
AR (1)	AR007626A1 (uk)
AT (1)	ATE229019T1 (uk)
AU (1)	AU711575B2 (uk)
BG (1)	BG63545B1 (uk)
BR (1)	BR9710002A (uk)
CA (1)	CA2258165C (uk)
CZ (1)	CZ297769B6 (uk)
DE (1)	DE69717627T2 (uk)
DK (1)	DK0907650T3 (uk)
EE (1)	EE03688B1 (uk)
ES (1)	ES2188957T3 (uk)
HU (1)	HU223093B1 (uk)
ID (1)	ID17275A (uk)
IL (1)	IL127740A (uk)
MY (1)	MY116917A (uk)
NO (1)	NO312102B1 (uk)
NZ (1)	NZ333382A (uk)
PL (1)	PL201704B1 (uk)
PT (1)	PT907650E (uk)
RU (1)	RU2190611C2 (uk)
SI (1)	SI0907650T1 (uk)
SK (1)	SK282769B6 (uk)
TR (1)	TR199802709T2 (uk)
TW (1)	TW490464B (uk)
UA (1)	UA53649C2 (uk)
WO (1)	WO1997049704A1 (uk)
ZA (1)	ZA975698B (uk)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU711575B2 (en) *	1996-06-27	1999-10-14	Janssen Pharmaceutica N.V.	N-(4-(Heteroarylmethyl)Phenyl)-Heteroarylamines
ES2224462T3 (es)	1997-12-11	2005-03-01	Janssen Pharmaceutica N.V.	Anilidas mimeticas del acido retinoico.
US6858598B1 (en)	1998-12-23	2005-02-22	G. D. Searle & Co.	Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US6833373B1 (en)	1998-12-23	2004-12-21	G.D. Searle & Co.	Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
DE19951701A1 (de)	1999-10-27	2001-05-03	Aventis Pharma Gmbh	Verwendung von 2-Imidazolyl-substituierten Carbinolen zur Herstellung eines Medikaments zur Behandlung oder Prophylaxe von durch ischämischen Zuständen bewirkten Krankheiten
US7780687B2 (en) *	2002-04-17	2010-08-24	Tyco Healthcare Group Lp	Method and apparatus for anastomosis including expandable anchor
AU2003284981B2 (en)	2002-10-30	2009-05-28	Merck Sharp & Dohme Corp.	Inhibitors of Akt activity
CN1809351A (zh)	2003-04-24	2006-07-26	麦克公司	Akt活性抑制剂
KR101218213B1 (ko) *	2003-07-03	2013-01-04	시토비아 인크.	카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린
US8309562B2 (en) *	2003-07-03	2012-11-13	Myrexis, Inc.	Compounds and therapeutical use thereof
DE10337942A1 (de) *	2003-08-18	2005-03-17	Merck Patent Gmbh	Aminobenzimidazolderivate
JP2008514601A (ja)	2004-09-24	2008-05-08	アラーガン、インコーポレイテッド	特異的α２アドレナリン作動剤としての４−（フェニルメチルおよび置換フェニルメチル）−イミダゾール−２−チオン
EP1791833A2 (en) *	2004-09-24	2007-06-06	Allergan, Inc.	4-(condensed cyclicmethyl)-imidazole-2-thiones acting as alpha2 adrenergic agonists
CA2581828A1 (en) *	2004-09-24	2006-04-06	Allergan, Inc.	4-(heteroaryl-methyl and substituted heteroaryl-methyl)-imidazole-2-thiones acting as alpha2 adrenergic agonists
AU2005290013A1 (en) *	2004-09-28	2006-04-06	Allergan, Inc.	Unsubstituted and substituted 4-benzyl-1,3-dihydro-imidazole-2-thiones acting as specific or selective alpha2 adrenergic agonists and methods for using the same
US8258145B2 (en) *	2005-01-03	2012-09-04	Myrexis, Inc.	Method of treating brain cancer
EP1833482A4 (en)	2005-01-03	2011-02-16	Myriad Genetics Inc	COMPOUNDS AND ITS THERAPEUTIC USE
US7547782B2 (en) *	2005-09-30	2009-06-16	Bristol-Myers Squibb Company	Met kinase inhibitors
AU2007207607B2 (en) *	2006-01-17	2012-04-19	Stiefel Laboratories, Inc.	Treatment of inflammatory disorders with triazole compounds
US8188124B2 (en)	2006-10-17	2012-05-29	Stiefel Laboratories, Inc.	Talarazole metabolites
US8133911B2 (en) *	2007-10-18	2012-03-13	Dompe S.P.A	(R)-4-(heteroaryl) phenylethyl derivatives and pharmaceutical compositions containing them
GB0811091D0 (en) *	2008-06-17	2008-07-23	Cancer Rec Tech Ltd	CYP26 Inhibitors
US10414760B2 (en)	2016-11-29	2019-09-17	Angion Biomedica Corp.	Cytochrome P450 inhibitors and uses thereof
CA2800664C (en)	2010-06-01	2019-09-24	Angion Biomedica Corp.	Benzothiazole cytochrome p450 inhibitors and therapeutic uses thereof
KR101108577B1 (ko) *	2010-07-28	2012-01-30	국제엘렉트릭코리아 주식회사	테이프 히터
PT2730564T (pt)	2010-11-19	2018-07-24	Ligand Pharm Inc	Aminas heterocíclicas e suas utilizações
US9248120B2 (en)	2011-08-23	2016-02-02	The Board Of Trustees Of The Leland Stanford Junior University	Reversing intestinal inflammation by inhibiting retinoic acid metabolism
CN107074841B (zh)	2014-08-11	2021-03-26	安吉恩生物医药公司	细胞色素p450抑制剂及其用途
US10287282B2 (en)	2014-12-31	2019-05-14	Angion Biomedica Corp.	Methods and agents for treating disease
US10807983B2 (en)	2015-03-16	2020-10-20	Ligand Pharmaceuticals, Inc.	Imidazo-fused heterocycles and uses thereof
CN106588780A (zh) *	2016-12-15	2017-04-26	青岛辰达生物科技有限公司	一种盐酸右美托咪定中间体的制备工艺
CN106632051A (zh) *	2016-12-15	2017-05-10	青岛辰达生物科技有限公司	一种盐酸右美托咪定中间体的合成方法
CN106588779A (zh) *	2016-12-15	2017-04-26	青岛辰达生物科技有限公司	一种合成盐酸右美托咪定中间体的方法
KR20210055340A (ko)	2019-11-07	2021-05-17	정화종	화물 커버
CN115462347B (zh) *	2021-08-13	2024-07-16	广州市妇女儿童医疗中心	视黄酸代谢通路在先天性巨结肠疾病中的应用

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1986002073A1 (fr) *	1984-10-03	1986-04-10	Takeda Chemical Industries, Ltd.	Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant
NZ221729A (en) *	1986-09-15	1989-07-27	Janssen Pharmaceutica Nv	Imidazolyl methyl-substituted benzimidazole derivatives and pharmaceutical compositions
CA2002859C (en) *	1988-11-29	1998-12-29	Jean P. F. Van Wauwe	Method of treating epithelial disorders
DK0482208T3 (da)	1990-04-25	2000-09-18	Nissan Chemical Ind Ltd	Pyridazinonderivat
ZW1992A1 (en) *	1991-02-25	1993-09-22	Janssen Pharmaceutica Nv	4-/(2-benzotiazolyl)methylamino/-b-/(3,4-difluorephenoxy)methyl/-1-piperidine ethanol
FR2677356B1 (fr) *	1991-06-05	1995-03-17	Sanofi Sa	Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant.
TW282469B (uk) *	1993-06-11	1996-08-01	Janssen Pharmaceutica Nv
TW321649B (uk)	1994-11-12	1997-12-01	Zeneca Ltd
US5582832A (en) *	1995-06-06	1996-12-10	Chesebrough-Pond's Usa Co., Division Of Conopco, Inc.	Compositions for topical application to skin
GB9624482D0 (en)	1995-12-18	1997-01-15	Zeneca Phaema S A	Chemical compounds
JP4471404B2 (ja)	1996-02-13	2010-06-02	アストラゼネカユーケイリミテッド	Ｖｅｇｆインヒビターとしてのキナゾリン誘導体
US5731342A (en) *	1996-02-22	1998-03-24	Eli Lilly And Company	Benzothiophenes, formulations containing same, and methods
AU711575B2 (en) *	1996-06-27	1999-10-14	Janssen Pharmaceutica N.V.	N-(4-(Heteroarylmethyl)Phenyl)-Heteroarylamines

1997
- 1997-06-19 AU AU34356/97A patent/AU711575B2/en not_active Expired
- 1997-06-19 KR KR10-1998-0709764A patent/KR100365312B1/ko not_active Expired - Lifetime
- 1997-06-19 TR TR1998/02709T patent/TR199802709T2/xx unknown
- 1997-06-19 EE EE9800437A patent/EE03688B1/xx unknown
- 1997-06-19 SI SI9730478T patent/SI0907650T1/xx unknown
- 1997-06-19 WO PCT/EP1997/003248 patent/WO1997049704A1/en not_active Ceased
- 1997-06-19 UA UA98116146A patent/UA53649C2/uk unknown
- 1997-06-19 HU HU9902138A patent/HU223093B1/hu active IP Right Grant
- 1997-06-19 PL PL330816A patent/PL201704B1/pl unknown
- 1997-06-19 BR BR9710002A patent/BR9710002A/pt not_active IP Right Cessation
- 1997-06-19 CA CA002258165A patent/CA2258165C/en not_active Expired - Lifetime
- 1997-06-19 PT PT97930378T patent/PT907650E/pt unknown
- 1997-06-19 ES ES97930378T patent/ES2188957T3/es not_active Expired - Lifetime
- 1997-06-19 AT AT97930378T patent/ATE229019T1/de active
- 1997-06-19 CN CN97195865A patent/CN1102593C/zh not_active Expired - Lifetime
- 1997-06-19 SK SK1781-98A patent/SK282769B6/sk not_active IP Right Cessation
- 1997-06-19 IL IL12774097A patent/IL127740A/en not_active IP Right Cessation
- 1997-06-19 JP JP50232198A patent/JP3404749B2/ja not_active Expired - Lifetime
- 1997-06-19 NZ NZ333382A patent/NZ333382A/xx not_active IP Right Cessation
- 1997-06-19 DK DK97930378T patent/DK0907650T3/da active
- 1997-06-19 RU RU99101902/04A patent/RU2190611C2/ru active
- 1997-06-19 DE DE69717627T patent/DE69717627T2/de not_active Expired - Lifetime
- 1997-06-19 EP EP97930378A patent/EP0907650B1/en not_active Expired - Lifetime
- 1997-06-19 CZ CZ0423198A patent/CZ297769B6/cs not_active IP Right Cessation
- 1997-06-19 US US09/214,080 patent/US6124330A/en not_active Expired - Lifetime
- 1997-06-23 TW TW086108726A patent/TW490464B/zh not_active IP Right Cessation
- 1997-06-25 MY MYPI97002859A patent/MY116917A/en unknown
- 1997-06-26 ID IDP972217A patent/ID17275A/id unknown
- 1997-06-26 ZA ZA975698A patent/ZA975698B/xx unknown
- 1997-06-26 AR ARP970102822A patent/AR007626A1/es active IP Right Grant
1998
- 1998-12-14 BG BG103013A patent/BG63545B1/bg unknown
- 1998-12-21 NO NO19986017A patent/NO312102B1/no not_active IP Right Cessation
2000
- 2000-07-25 US US09/624,966 patent/US6486187B1/en not_active Expired - Lifetime
2002
- 2002-09-10 US US10/238,686 patent/US6833375B2/en not_active Expired - Lifetime
2004
- 2004-11-02 US US10/979,362 patent/US7205312B2/en not_active Expired - Fee Related
2006
- 2006-12-13 US US11/639,043 patent/US7378433B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HUP9902138A2 (hu)	1999-10-28
NZ333382A (en)	2000-05-26
JP3404749B2 (ja)	2003-05-12
AU3435697A (en)	1998-01-14
JP2000503670A (ja)	2000-03-28
US7205312B2 (en)	2007-04-17
HUP9902138A3 (en)	2001-10-29
DE69717627D1 (de)	2003-01-16
CA2258165A1 (en)	1997-12-31
EE03688B1 (et)	2002-04-15
HU223093B1 (hu)	2004-03-29
ID17275A (id)	1997-12-18
EE9800437A (et)	1999-06-15
AU711575B2 (en)	1999-10-14
BR9710002A (pt)	1999-08-10
CN1223654A (zh)	1999-07-21
AR007626A1 (es)	1999-11-10
US6833375B2 (en)	2004-12-21
KR20000016196A (ko)	2000-03-25
SK282769B6 (sk)	2002-12-03
NO986017D0 (no)	1998-12-21
IL127740A0 (en)	1999-10-28
IL127740A (en)	2001-09-13
EP0907650B1 (en)	2002-12-04
BG103013A (en)	1999-09-30
NO312102B1 (no)	2002-03-18
TR199802709T2 (xx)	1999-02-22
TW490464B (en)	2002-06-11
CN1102593C (zh)	2003-03-05
US6486187B1 (en)	2002-11-26
PL330816A1 (en)	1999-06-07
US20050113378A1 (en)	2005-05-26
HK1018458A1 (en)	1999-12-24
PL201704B1 (pl)	2009-04-30
ES2188957T3 (es)	2003-07-01
CZ297769B6 (cs)	2007-03-28
UA53649C2 (uk)	2003-02-17
MY116917A (en)	2004-04-30
EP0907650A1 (en)	1999-04-14
SI0907650T1 (en)	2003-06-30
CZ423198A3 (cs)	1999-05-12
WO1997049704A1 (en)	1997-12-31
RU2190611C2 (ru)	2002-10-10
US7378433B2 (en)	2008-05-27
US6124330A (en)	2000-09-26
DK0907650T3 (da)	2003-03-10
NO986017L (no)	1999-02-19
ZA975698B (en)	1999-01-20
DE69717627T2 (de)	2003-09-18
US20030176419A1 (en)	2003-09-18
US20070088062A1 (en)	2007-04-19
SK178198A3 (en)	2000-05-16
CA2258165C (en)	2009-03-03
ATE229019T1 (de)	2002-12-15
KR100365312B1 (ko)	2003-03-06
PT907650E (pt)	2003-04-30

Publication	Publication Date	Title
BG63545B1 (bg)	2002-04-30	N-[4-(хетероарилметил)фенил]-хетероариламини
US7579352B2 (en)	2009-08-25	Retinoic acid mimetic anilides
JP2003513090A (ja)	2003-04-08	Ｎ置換カルバモイルオキシアルキルアゾリウム誘導体
CZ20002156A3 (cs)	2000-10-11	Mimetické anilidy kyseliny retinoové
HK1018458B (en)	2003-03-21	N-4-(heteroarylmethyl)phenyl]-heteroarylamines
CA2236834A1 (en)	1997-05-29	Piperidine and tetrahydropyridine derivatives