CA2953284A1 - Methods for the preparation of 1,3-benzodioxole heterocyclic compounds - Google Patents
Methods for the preparation of 1,3-benzodioxole heterocyclic compounds Download PDFInfo
- Publication number
- CA2953284A1 CA2953284A1 CA2953284A CA2953284A CA2953284A1 CA 2953284 A1 CA2953284 A1 CA 2953284A1 CA 2953284 A CA2953284 A CA 2953284A CA 2953284 A CA2953284 A CA 2953284A CA 2953284 A1 CA2953284 A1 CA 2953284A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- hydrogen
- chloro
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- -1 1,3-benzodioxole heterocyclic compounds Chemical class 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001246 bromo group Chemical group Br* 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N NMP Substances CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 12
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical group C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 8
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 229910052604 silicate mineral Inorganic materials 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 239000000543 intermediate Substances 0.000 abstract description 21
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 abstract description 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000008346 aqueous phase Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000013019 agitation Methods 0.000 description 15
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- VCONERRCKOKCHE-UHFFFAOYSA-N 1-(2,3-dihydroxy-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(O)=C1O VCONERRCKOKCHE-UHFFFAOYSA-N 0.000 description 10
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052901 montmorillonite Inorganic materials 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 3
- 238000012369 In process control Methods 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010965 in-process control Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
- HOVYYZPIMOIDPH-UHFFFAOYSA-N 1-(7-methoxyspiro[1,3-benzodioxole-2,4'-thiane]-4-yl)ethanone Chemical compound COC1=CC=C(C(C)=O)C2=C1OC1(CCSCC1)O2 HOVYYZPIMOIDPH-UHFFFAOYSA-N 0.000 description 2
- KKWRVUBDCJQHBZ-UHFFFAOYSA-N 3,4,5-trichloropyridine Chemical compound ClC1=CN=CC(Cl)=C1Cl KKWRVUBDCJQHBZ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229940000406 drug candidate Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010583 slow cooling Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- 150000005529 1,3-benzodioxoles Chemical class 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- CPLBLSLTYWIYLY-UHFFFAOYSA-N 1-tert-butylsulfanyl-2-methylbenzene Chemical compound CC1=CC=CC=C1SC(C)(C)C CPLBLSLTYWIYLY-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- ZSBNXOIAJFVXMP-UHFFFAOYSA-N 5-tert-butyl-2-methylbenzenethiol Chemical compound CC1=CC=C(C(C)(C)C)C=C1S ZSBNXOIAJFVXMP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- 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
- C07D495/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14173397 | 2014-06-23 | ||
| EP14173397.2 | 2014-06-23 | ||
| PCT/EP2015/063942 WO2015197534A2 (en) | 2014-06-23 | 2015-06-22 | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2953284A1 true CA2953284A1 (en) | 2015-12-30 |
Family
ID=50980952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2953284A Abandoned CA2953284A1 (en) | 2014-06-23 | 2015-06-22 | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9908894B2 (OSRAM) |
| EP (1) | EP3157930B1 (OSRAM) |
| JP (1) | JP6785666B2 (OSRAM) |
| KR (1) | KR20170016894A (OSRAM) |
| CN (1) | CN106459081B (OSRAM) |
| AU (1) | AU2015279428B2 (OSRAM) |
| BR (1) | BR112016029510A2 (OSRAM) |
| CA (1) | CA2953284A1 (OSRAM) |
| DK (1) | DK3157930T3 (OSRAM) |
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| WO (1) | WO2015197534A2 (OSRAM) |
| ZA (1) | ZA201608442B (OSRAM) |
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| CA3007432A1 (en) * | 2015-12-18 | 2017-06-22 | Leo Pharma A/S | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
| WO2018234299A1 (en) * | 2017-06-20 | 2018-12-27 | Leo Pharma A/S | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
| CN111727191B (zh) | 2017-12-15 | 2024-01-05 | 联合疗法公司 | 取代的氮杂环丁烷二氢噻吩并吡啶类化合物及其作为磷酸二酯酶抑制剂的用途 |
| USD914676S1 (en) | 2018-05-11 | 2021-03-30 | Samsung Electronics Co., Ltd. | Notebook computer |
| IL284815B2 (en) | 2019-01-15 | 2025-10-01 | Union Therapeutics As | Modified-release tablet formulations containing phosphodiesterase inhibitors |
| AU2022245186A1 (en) | 2021-03-22 | 2023-10-05 | UNION therapeutics A/S | Treatment of hidradenitis suppurativa with orismilast |
| GB202205715D0 (en) | 2022-04-19 | 2022-06-01 | Union Therapeutics As | Treatment of neutrophilic dermatoses |
| GB202306663D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Combination therapy |
| GB202306662D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Dosage regimen |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6514996B2 (en) * | 1995-05-19 | 2003-02-04 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxole |
| AU705690B2 (en) * | 1995-05-19 | 1999-05-27 | Kyowa Hakko Kogyo Co. Ltd. | Oxygen-containing heterocyclic compounds |
| DE10205274A1 (de) * | 2002-02-08 | 2003-08-21 | Boehringer Ingelheim Pharma | Neue Arzneimittelkompositionen enthaltend neben Anticholinergika heterocyclische Verbindungen |
| US20050245750A1 (en) * | 2002-07-03 | 2005-11-03 | Kyowa Hakko Kogyo Co., Ltd. | Process for preparing 1,3-benzodioxole-2-spirocycloalkane derivative |
| CN101490004B (zh) * | 2006-07-14 | 2012-01-11 | 奇斯药制品公司 | 作为磷酸二酯酶抑制剂的1-苯基-2-吡啶基烯基醇的衍生物 |
| KR101507717B1 (ko) | 2006-12-22 | 2015-04-08 | 레오 파마 에이/에스 | Ｐｄｅ4 억제제로서 유용한 치환된 아세토페논 |
| UA98639C2 (en) * | 2007-02-28 | 2012-06-11 | Лео Фарма А/С | Phosphodiesterase inhibitors |
| JP5501770B2 (ja) * | 2007-02-28 | 2014-05-28 | レオ ファーマ アクティーゼルスカブ | 新規ホスホジエステラーゼ阻害剤 |
| UA109140C2 (uk) * | 2010-06-24 | 2015-07-27 | Гетероциклічні сполуки бензодіоксолу або бензодіоксепіну як інгібітори фосфодіестераз | |
| WO2014096018A1 (en) * | 2012-12-19 | 2014-06-26 | Leo Pharma A/S | Methods for the preparation of substituted acetophenones |
| CA3007432A1 (en) * | 2015-12-18 | 2017-06-22 | Leo Pharma A/S | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
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2015
- 2015-06-22 CA CA2953284A patent/CA2953284A1/en not_active Abandoned
- 2015-06-22 PT PT15730183T patent/PT3157930T/pt unknown
- 2015-06-22 DK DK15730183.9T patent/DK3157930T3/en active
- 2015-06-22 WO PCT/EP2015/063942 patent/WO2015197534A2/en not_active Ceased
- 2015-06-22 ES ES15730183T patent/ES2702451T3/es active Active
- 2015-06-22 TW TW104120096A patent/TW201613934A/zh unknown
- 2015-06-22 RU RU2017101808A patent/RU2697251C2/ru active
- 2015-06-22 EP EP15730183.9A patent/EP3157930B1/en active Active
- 2015-06-22 KR KR1020167037002A patent/KR20170016894A/ko not_active Withdrawn
- 2015-06-22 PL PL15730183T patent/PL3157930T3/pl unknown
- 2015-06-22 CN CN201580033483.8A patent/CN106459081B/zh active Active
- 2015-06-22 MX MX2016016378A patent/MX2016016378A/es unknown
- 2015-06-22 AU AU2015279428A patent/AU2015279428B2/en not_active Ceased
- 2015-06-22 BR BR112016029510A patent/BR112016029510A2/pt not_active IP Right Cessation
- 2015-06-22 US US15/320,227 patent/US9908894B2/en active Active
- 2015-06-22 JP JP2016572800A patent/JP6785666B2/ja active Active
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2016
- 2016-12-01 IL IL249336A patent/IL249336A0/en unknown
- 2016-12-07 ZA ZA2016/08442A patent/ZA201608442B/en unknown
Also Published As
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|---|---|
| AU2015279428A1 (en) | 2017-01-05 |
| BR112016029510A2 (pt) | 2017-08-22 |
| JP6785666B2 (ja) | 2020-11-18 |
| ES2702451T3 (es) | 2019-03-01 |
| TW201613934A (en) | 2016-04-16 |
| KR20170016894A (ko) | 2017-02-14 |
| WO2015197534A3 (en) | 2016-03-17 |
| CN106459081B (zh) | 2019-09-10 |
| PL3157930T3 (pl) | 2019-04-30 |
| EP3157930A2 (en) | 2017-04-26 |
| MX2016016378A (es) | 2017-10-16 |
| US9908894B2 (en) | 2018-03-06 |
| CN106459081A (zh) | 2017-02-22 |
| US20170137438A1 (en) | 2017-05-18 |
| RU2017101808A3 (OSRAM) | 2019-01-22 |
| WO2015197534A2 (en) | 2015-12-30 |
| IL249336A0 (en) | 2017-02-28 |
| JP2017520547A (ja) | 2017-07-27 |
| DK3157930T3 (en) | 2019-01-21 |
| RU2697251C2 (ru) | 2019-08-13 |
| PT3157930T (pt) | 2018-12-24 |
| EP3157930B1 (en) | 2018-10-17 |
| AU2015279428B2 (en) | 2018-02-15 |
| ZA201608442B (en) | 2018-05-30 |
| RU2017101808A (ru) | 2018-07-27 |
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