IL127740A - N - [- 4 (Troerylmethyl) phenyl] - the troarylamines, N - their oxides, their preparation, and pharmaceutical preparations containing them - Google Patents

N - [- 4 (Troerylmethyl) phenyl] - the troarylamines, N - their oxides, their preparation, and pharmaceutical preparations containing them

Info

Publication number: IL127740A
Authority: IL; Israel
Prior art keywords: formula; amino; aryl; alkyl; compound
Prior art date: 1996-06-27

Application number

IL12774097A

Other languages

English (en)

Hebrew (he)

Other versions

IL127740A0 (en

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.)

1996-06-27

Filing date

1997-06-19

Publication date

2001-09-13

1997-06-19 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1999-10-28 Publication of IL127740A0 publication Critical patent/IL127740A0/xx

2001-09-13 Publication of IL127740A publication Critical patent/IL127740A/en

Links

125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 45
238000002360 preparation method Methods 0.000 title claims description 24
239000008194 pharmaceutical composition Substances 0.000 title description 5
239000000203 mixture Substances 0.000 claims description 154
-1 CMalkyloxy Chemical group 0.000 claims description 137
150000001875 compounds Chemical class 0.000 claims description 137
239000002904 solvent Substances 0.000 claims description 77
125000003118 aryl group Chemical group 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 27
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
150000002431 hydrogen Chemical group 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
239000012442 inert solvent Substances 0.000 claims description 18
239000002585 base Substances 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
208000035475 disorder Diseases 0.000 claims description 15
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
150000001204 N-oxides Chemical class 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000003153 chemical reaction reagent Substances 0.000 claims description 10
230000003780 keratinization Effects 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
229960005084 calcitriol Drugs 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 7
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
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 claims description 7
239000011612 calcitriol Substances 0.000 claims description 7
235000020964 calcitriol Nutrition 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
201000004681 Psoriasis Diseases 0.000 claims description 6
125000004104 aryloxy group Chemical group 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
239000003937 drug carrier Substances 0.000 claims description 6
125000004193 piperazinyl group Chemical group 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
125000000623 heterocyclic group Chemical group 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
239000000651 prodrug Substances 0.000 claims description 5
229940002612 prodrug Drugs 0.000 claims description 5
125000005110 aryl thio group Chemical group 0.000 claims 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 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 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
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 3
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 3
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 3
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
229910021645 metal ion Inorganic materials 0.000 claims description 2
YJZUQRIWMVAQQP-UHFFFAOYSA-N n-[4-[cyclohexyl(imidazol-1-yl)methyl]phenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCCCC1C(N1C=NC=C1)C(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YJZUQRIWMVAQQP-UHFFFAOYSA-N 0.000 claims description 2
230000001575 pathological effect Effects 0.000 claims description 2
125000002265 phtalazinyl group Chemical group 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000002294 quinazolinyl group Chemical group N1=C(N=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
230000009466 transformation Effects 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 15
125000001475 halogen functional group Chemical group 0.000 claims 7
125000000815 N-oxide group Chemical group 0.000 claims 1
125000002619 bicyclic group Chemical group 0.000 claims 1
238000011260 co-administration Methods 0.000 claims 1
125000002950 monocyclic group Chemical group 0.000 claims 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
238000000844 transformation Methods 0.000 claims 1
239000000543 intermediate Substances 0.000 description 82
239000000243 solution Substances 0.000 description 63
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
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 56
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
229910001868 water Inorganic materials 0.000 description 40
239000012044 organic layer Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
239000002244 precipitate Substances 0.000 description 31
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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 26
238000004440 column chromatography Methods 0.000 description 23
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
229960001727 tretinoin Drugs 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
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 18
229930002330 retinoic acid Natural products 0.000 description 18
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 15
235000011114 ammonium hydroxide Nutrition 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
229960004132 diethyl ether Drugs 0.000 description 11
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 11
230000000694 effects Effects 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 11
239000008213 purified water Substances 0.000 description 11
108010037444 diisopropylglutathione ester Proteins 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
235000015320 potassium carbonate Nutrition 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000003826 tablet Substances 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
241001465754 Metazoa Species 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
238000002156 mixing Methods 0.000 description 6
210000003491 skin Anatomy 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000012360 testing method Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
230000002159 abnormal effect Effects 0.000 description 5
GHQPBDDZGPAVJP-UHFFFAOYSA-N azanium;methanol;hydroxide Chemical compound N.O.OC GHQPBDDZGPAVJP-UHFFFAOYSA-N 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
230000004060 metabolic process Effects 0.000 description 5
239000002674 ointment Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
241000700159 Rattus Species 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000006071 cream Substances 0.000 description 4
230000004069 differentiation Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
238000004811 liquid chromatography Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 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
229910052757 nitrogen Inorganic materials 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-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
230000001225 therapeutic effect Effects 0.000 description 4
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-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
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
206010006187 Breast cancer Diseases 0.000 description 3
208000026310 Breast neoplasm Diseases 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
229960004217 benzyl alcohol Drugs 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000002124 endocrine Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000006210 lotion Substances 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
239000002207 metabolite Substances 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
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
UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 2
208000002874 Acne Vulgaris Diseases 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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206010008570 Chloasma Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
TXHUMRBWIWWBGW-UHFFFAOYSA-N Estradiol undecylate Natural products C1CC2=CC(O)=CC=C2C2C1C1CCC(OC(=O)CCCCCCCCCC)C1(C)CC2 TXHUMRBWIWWBGW-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
230000005526 G1 to G0 transition Effects 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229910017974 NH40H Inorganic materials 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
206010000496 acne Diseases 0.000 description 2
230000009471 action Effects 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
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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

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Public Health (AREA)
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Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL12774097A 1996-06-27 1997-06-19 N - [- 4 (Troerylmethyl) phenyl] - the troarylamines, N - their oxides, their preparation, and pharmaceutical preparations containing them IL127740A (en)

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
IL127740A0 IL127740A0 (en)	1999-10-28
IL127740A true IL127740A (en)	2001-09-13

Family

ID=8224119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12774097A IL127740A (en)	1996-06-27	1997-06-19	N - [- 4 (Troerylmethyl) phenyl] - the troarylamines, N - their oxides, their preparation, and pharmaceutical preparations containing them

Country Status (32)

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

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AU2007311026B2 (en)	2006-10-17	2012-05-17	Stiefel Laboratories, Inc.	Talarazole metabolites
WO2009050258A1 (en) *	2007-10-18	2009-04-23	Dompé 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
EP2576544A4 (en)	2010-06-01	2013-09-11	Angion Biomedica Corp	INHIBITORS OF CYTOCHROMES P450 AND USES THEREOF
US10414760B2 (en)	2016-11-29	2019-09-17	Angion Biomedica Corp.	Cytochrome P450 inhibitors and uses thereof
KR101108577B1 (ko) *	2010-07-28	2012-01-30	국제엘렉트릭코리아 주식회사	테이프 히터
EP3357915A1 (en)	2010-11-19	2018-08-08	Ligand Pharmaceuticals Inc.	Heterocycle amines with anti-inflammatory activity
WO2013028771A1 (en)	2011-08-23	2013-02-28	Leong Hwei Xian	Reversing intestinal inflammation by inhibiting retinoic acid metabolism
DK3180335T3 (da)	2014-08-11	2021-08-09	Angion Biomedica Corp	Cytokrom-p450-inhibitorer og anvendelser deraf
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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
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1997
- 1997-06-19 KR KR10-1998-0709764A patent/KR100365312B1/ko not_active Expired - Lifetime
- 1997-06-19 JP JP50232198A patent/JP3404749B2/ja not_active Expired - Lifetime
- 1997-06-19 AU AU34356/97A patent/AU711575B2/en not_active Expired
- 1997-06-19 RU RU99101902/04A patent/RU2190611C2/ru active
- 1997-06-19 CZ CZ0423198A patent/CZ297769B6/cs not_active IP Right Cessation
- 1997-06-19 HU HU9902138A patent/HU223093B1/hu active IP Right Grant
- 1997-06-19 AT AT97930378T patent/ATE229019T1/de active
- 1997-06-19 DK DK97930378T patent/DK0907650T3/da active
- 1997-06-19 TR TR1998/02709T patent/TR199802709T2/xx unknown
- 1997-06-19 EP EP97930378A patent/EP0907650B1/en not_active Expired - Lifetime
- 1997-06-19 EE EE9800437A patent/EE03688B1/xx unknown
- 1997-06-19 WO PCT/EP1997/003248 patent/WO1997049704A1/en not_active Ceased
- 1997-06-19 CN CN97195865A patent/CN1102593C/zh not_active Expired - Lifetime
- 1997-06-19 US US09/214,080 patent/US6124330A/en not_active Expired - Lifetime
- 1997-06-19 NZ NZ333382A patent/NZ333382A/xx not_active IP Right Cessation
- 1997-06-19 ES ES97930378T patent/ES2188957T3/es not_active Expired - Lifetime
- 1997-06-19 IL IL12774097A patent/IL127740A/en not_active IP Right Cessation
- 1997-06-19 UA UA98116146A patent/UA53649C2/uk unknown
- 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 SI SI9730478T patent/SI0907650T1/xx unknown
- 1997-06-19 SK SK1781-98A patent/SK282769B6/sk not_active IP Right Cessation
- 1997-06-19 DE DE69717627T patent/DE69717627T2/de not_active Expired - Lifetime
- 1997-06-19 CA CA002258165A patent/CA2258165C/en not_active Expired - Lifetime
- 1997-06-19 PT PT97930378T patent/PT907650E/pt unknown
- 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 ZA ZA975698A patent/ZA975698B/xx unknown
- 1997-06-26 ID IDP972217A patent/ID17275A/id 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
IL127740A0 (en)	1999-10-28
SK178198A3 (en)	2000-05-16
AU3435697A (en)	1998-01-14
MY116917A (en)	2004-04-30
US20050113378A1 (en)	2005-05-26
RU2190611C2 (ru)	2002-10-10
SI0907650T1 (en)	2003-06-30
SK282769B6 (sk)	2002-12-03
HUP9902138A2 (hu)	1999-10-28
ATE229019T1 (de)	2002-12-15
HU223093B1 (hu)	2004-03-29
PL330816A1 (en)	1999-06-07
BG103013A (en)	1999-09-30
US20070088062A1 (en)	2007-04-19
CZ297769B6 (cs)	2007-03-28
HK1018458A1 (en)	1999-12-24
ES2188957T3 (es)	2003-07-01
EP0907650A1 (en)	1999-04-14
KR100365312B1 (ko)	2003-03-06
PL201704B1 (pl)	2009-04-30
AU711575B2 (en)	1999-10-14
UA53649C2 (uk)	2003-02-17
NZ333382A (en)	2000-05-26
CN1102593C (zh)	2003-03-05
CN1223654A (zh)	1999-07-21
EP0907650B1 (en)	2002-12-04
US7378433B2 (en)	2008-05-27
NO986017D0 (no)	1998-12-21
EE9800437A (et)	1999-06-15
HUP9902138A3 (en)	2001-10-29
DK0907650T3 (da)	2003-03-10
CA2258165A1 (en)	1997-12-31
CZ423198A3 (cs)	1999-05-12
BR9710002A (pt)	1999-08-10
AR007626A1 (es)	1999-11-10
KR20000016196A (ko)	2000-03-25
ID17275A (id)	1997-12-18
EE03688B1 (et)	2002-04-15
US6833375B2 (en)	2004-12-21
TR199802709T2 (xx)	1999-02-22
US6486187B1 (en)	2002-11-26
US7205312B2 (en)	2007-04-17
DE69717627D1 (de)	2003-01-16
NO986017L (no)	1999-02-19
WO1997049704A1 (en)	1997-12-31
PT907650E (pt)	2003-04-30
CA2258165C (en)	2009-03-03
JP2000503670A (ja)	2000-03-28
US6124330A (en)	2000-09-26
US20030176419A1 (en)	2003-09-18
JP3404749B2 (ja)	2003-05-12
NO312102B1 (no)	2002-03-18
TW490464B (en)	2002-06-11
BG63545B1 (bg)	2002-04-30
ZA975698B (en)	1999-01-20
DE69717627T2 (de)	2003-09-18

Publication	Publication Date	Title
EP0907650B1 (en)	2002-12-04	N- 4-(heteroarylmethyl)phenyl]-heteroarylamines
EP1037880B1 (en)	2004-06-30	Retinoic acid mimetic anilides
AU698199B2 (en)	1998-10-29	6-{triazolyl{3-(trifluoromethyl)phenyl}methyl}-2- quinolinones and -quinolinethiones
HK1018458B (en)	2003-03-21	N-4-(heteroarylmethyl)phenyl]-heteroarylamines

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Date	Code	Title
2003-07-31	KB	Patent renewed
2007-07-24	KB	Patent renewed
2015-05-31	KB	Patent renewed
2018-01-31	EXP	Patent expired