CA2953284A1 - Methods for the preparation of 1,3-benzodioxole heterocyclic compounds - Google Patents

Methods for the preparation of 1,3-benzodioxole heterocyclic compounds Download PDF

Info

Publication number: CA2953284A1
Authority: CA; Canada
Prior art keywords: formula; compound; hydrogen; chloro; alkyl
Prior art date: 2014-06-23
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

Application number

CA2953284A

Other languages

English (en)

French (fr)

Inventor

Bjorn Metzler

Andre Faldt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Leo Pharma AS

Original Assignee

Leo Pharma AS

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.)

2014-06-23

Filing date

2015-06-22

Publication date

2015-12-30

2015-06-22 Application filed by Leo Pharma AS filed Critical Leo Pharma AS

2015-12-30 Publication of CA2953284A1 publication Critical patent/CA2953284A1/en

Status Abandoned legal-status Critical Current

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)

CA2953284A 2014-06-23 2015-06-22 Methods for the preparation of 1,3-benzodioxole heterocyclic compounds Abandoned CA2953284A1 (en)

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 (2)
EP (1)	EP3157930B1 (2)
JP (1)	JP6785666B2 (2)
KR (1)	KR20170016894A (2)
CN (1)	CN106459081B (2)
AU (1)	AU2015279428B2 (2)
BR (1)	BR112016029510A2 (2)
CA (1)	CA2953284A1 (2)
DK (1)	DK3157930T3 (2)
ES (1)	ES2702451T3 (2)
IL (1)	IL249336A0 (2)
MX (1)	MX2016016378A (2)
PL (1)	PL3157930T3 (2)
PT (1)	PT3157930T (2)
RU (1)	RU2697251C2 (2)
TW (1)	TW201613934A (2)
WO (1)	WO2015197534A2 (2)
ZA (1)	ZA201608442B (2)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI732808B (zh) *	2015-12-18	2021-07-11	丹麥商理奧藥品公司	1,3－苯并二氧雜環戊烯雜環化合物之製備方法
WO2018234299A1 (en) *	2017-06-20	2018-12-27	Leo Pharma A/S	Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
ES2935615T3 (es)	2017-12-15	2023-03-08	Union Therapeutics As	Azetidina dihidrotienopiridinas sustituidas y su uso como inhibidores de la fosfodiesterasa
USD914676S1 (en)	2018-05-11	2021-03-30	Samsung Electronics Co., Ltd.	Notebook computer
BR112021013675A2 (pt)	2019-01-15	2021-09-14	UNION therapeutics A/S	Formulações de comprimido de liberação modificada que contêm inibidores de fosfodiesterase
EP4313043A1 (en)	2021-03-22	2024-02-07	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)

* Cited by examiner, † Cited by third party
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
DK0771794T3 (da) *	1995-05-19	2006-09-11	Kyowa Hakko Kogyo Kk	Oxygenholdige heterocykliske forbindelser
DE10205274A1 (de) *	2002-02-08	2003-08-21	Boehringer Ingelheim Pharma	Neue Arzneimittelkompositionen enthaltend neben Anticholinergika heterocyclische Verbindungen
AU2003252467A1 (en) *	2002-07-03	2004-01-23	Kyowa Hakko Kogyo Co., Ltd.	Process for preparation of 1,3-benzodioxole-2-spiro- cycloalkane derivatives
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
DE602007013617D1 (de)	2006-12-22	2011-05-12	Leo Pharma As	Als pde4-inhibitoren geeignete substituierte acetophenone
RS53407B (sr) *	2007-02-28	2014-10-31	Leo Pharma A/S	Novi inhibitori fosfodiesteraze
UA98639C2 (en) *	2007-02-28	2012-06-11	Лео Фарма А/С	Phosphodiesterase inhibitors
KR101864578B1 (ko) *	2010-06-24	2018-06-07	레오 파마 에이/에스	포스포디에스테라제 억제제로서의 벤조디옥솔 또는 벤조디옥세핀 헤테로사이클릭 화합물
WO2014096018A1 (en) *	2012-12-19	2014-06-26	Leo Pharma A/S	Methods for the preparation of substituted acetophenones
TWI732808B (zh) *	2015-12-18	2021-07-11	丹麥商理奧藥品公司	1,3－苯并二氧雜環戊烯雜環化合物之製備方法

2015
- 2015-06-22 AU AU2015279428A patent/AU2015279428B2/en not_active Ceased
- 2015-06-22 EP EP15730183.9A patent/EP3157930B1/en active Active
- 2015-06-22 PL PL15730183T patent/PL3157930T3/pl unknown
- 2015-06-22 ES ES15730183T patent/ES2702451T3/es active Active
- 2015-06-22 CN CN201580033483.8A patent/CN106459081B/zh active Active
- 2015-06-22 PT PT15730183T patent/PT3157930T/pt unknown
- 2015-06-22 TW TW104120096A patent/TW201613934A/zh unknown
- 2015-06-22 JP JP2016572800A patent/JP6785666B2/ja active Active
- 2015-06-22 US US15/320,227 patent/US9908894B2/en active Active
- 2015-06-22 CA CA2953284A patent/CA2953284A1/en not_active Abandoned
- 2015-06-22 MX MX2016016378A patent/MX2016016378A/es unknown
- 2015-06-22 DK DK15730183.9T patent/DK3157930T3/en active
- 2015-06-22 BR BR112016029510A patent/BR112016029510A2/pt not_active IP Right Cessation
- 2015-06-22 RU RU2017101808A patent/RU2697251C2/ru active
- 2015-06-22 WO PCT/EP2015/063942 patent/WO2015197534A2/en not_active Ceased
- 2015-06-22 KR KR1020167037002A patent/KR20170016894A/ko not_active Withdrawn
2016
- 2016-12-01 IL IL249336A patent/IL249336A0/en unknown
- 2016-12-07 ZA ZA2016/08442A patent/ZA201608442B/en unknown

Also Published As

Publication number	Publication date
KR20170016894A (ko)	2017-02-14
CN106459081A (zh)	2017-02-22
MX2016016378A (es)	2017-10-16
EP3157930A2 (en)	2017-04-26
JP2017520547A (ja)	2017-07-27
RU2697251C2 (ru)	2019-08-13
US20170137438A1 (en)	2017-05-18
CN106459081B (zh)	2019-09-10
AU2015279428B2 (en)	2018-02-15
RU2017101808A3 (2)	2019-01-22
ES2702451T3 (es)	2019-03-01
PL3157930T3 (pl)	2019-04-30
PT3157930T (pt)	2018-12-24
IL249336A0 (en)	2017-02-28
DK3157930T3 (en)	2019-01-21
AU2015279428A1 (en)	2017-01-05
TW201613934A (en)	2016-04-16
JP6785666B2 (ja)	2020-11-18
RU2017101808A (ru)	2018-07-27
BR112016029510A2 (pt)	2017-08-22
WO2015197534A3 (en)	2016-03-17
US9908894B2 (en)	2018-03-06
ZA201608442B (en)	2018-05-30
WO2015197534A2 (en)	2015-12-30
EP3157930B1 (en)	2018-10-17

Legal Events

Date	Code	Title	Description
2020-11-07	FZDE	Discontinued	Effective date: 20200831

Publication	Publication Date	Title
CA2953284A1 (en)	2015-12-30	Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
RU2430092C2 (ru)	2011-09-27	Способ получения телмисартана
ES2585221T3 (es)	2016-10-04	Un proceso para la preparación de 6-(7-((1-aminociclopropil)metoxi)-6-metoxiquinolin-4-iloxi)-n-metil-1-naftamida y productos intermedios sintéticos de la misma
JP6934872B2 (ja)	2021-09-15	１，３−ベンゾジオキソール複素環化合物の製造方法
AU2018286964B2 (en)	2022-04-14	Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
CN107089982B (zh)	2018-06-05	4，5-二取代-1-氢-吡咯(2，3-f)喹啉-2，7，9-三羧酸酯化合物及应用
JP7237385B2 (ja)	2023-03-13	３－ブロモ－５－（２－エチルイミダゾ［１，２－ａ］ピリジン－３－カルボニル）－２－ヒドロキシベンゾニトリルの合成
JPH09124558A (ja)	1997-05-13	スクシニルコハク酸ジアルキルの調製法
HK1231056A1 (en)	2017-12-15	Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
JP2019151578A (ja)	2019-09-12	ビフェニル−２−カルボン酸メチルエステルの製造方法
JP2006315979A (ja)	2006-11-24	２−アルキル−ベンゾチアゾール類の製造方法
JP2001002650A (ja)	2001-01-09	２，２’，４，４’，５，５’−ヘキサアリルビイミダゾールの製造方法