RU2018107689A - Способ синтеза равидасвира - Google Patents

Способ синтеза равидасвира Download PDF

Info

Publication number: RU2018107689A
Authority: RU; Russia
Prior art keywords: formula; group; solvent; compound; base
Prior art date: 2015-08-03

Application number

RU2018107689A

Other languages

English (en)

Russian (ru)

Other versions

RU2018107689A3 (es

Inventor

Грациано Кастальди

Алессандро БАРУТО

Эрминио ОЛЬДАНИ

Мауро ГАБОАРДИ

Original Assignee

Хс-Фарма Аг

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.)

2015-08-03

Filing date

2016-07-28

Publication date

2019-09-05

2016-07-28 Application filed by Хс-Фарма Аг filed Critical Хс-Фарма Аг

2019-09-05 Publication of RU2018107689A publication Critical patent/RU2018107689A/ru

2019-12-24 Publication of RU2018107689A3 publication Critical patent/RU2018107689A3/ru

Links

238000000034 method Methods 0.000 title claims 16
230000015572 biosynthetic process Effects 0.000 title claims 2
LCHMHYPWGWYXEL-ZYADHFCISA-N methyl n-[(2s)-1-[(2s)-2-[5-[6-[2-[(2s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]naphthalen-2-yl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=C3C=CC(=CC3=CC=2)C=2C=C3NC(=NC3=CC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)N1 LCHMHYPWGWYXEL-ZYADHFCISA-N 0.000 title claims 2
229950007950 ravidasvir Drugs 0.000 title claims 2
238000003786 synthesis reaction Methods 0.000 title claims 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 27
150000001875 compounds Chemical class 0.000 claims 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 21
239000002904 solvent Substances 0.000 claims 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 12
239000003054 catalyst Substances 0.000 claims 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 11
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 9
239000003795 chemical substances by application Substances 0.000 claims 9
NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 8
125000005843 halogen group Chemical group 0.000 claims 6
229910052763 palladium Inorganic materials 0.000 claims 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
125000000217 alkyl group Chemical group 0.000 claims 4
229910052796 boron Inorganic materials 0.000 claims 4
239000003153 chemical reaction reagent Substances 0.000 claims 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
229910000029 sodium carbonate Inorganic materials 0.000 claims 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical group FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 4
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
239000011230 binding agent Substances 0.000 claims 3
125000001246 bromo group Chemical group Br* 0.000 claims 3
125000003827 glycol group Chemical group 0.000 claims 3
230000003993 interaction Effects 0.000 claims 3
239000000203 mixture Substances 0.000 claims 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
150000007524 organic acids Chemical class 0.000 claims 3
235000011056 potassium acetate Nutrition 0.000 claims 3
125000003107 substituted aryl group Chemical group 0.000 claims 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
229910052794 bromium Inorganic materials 0.000 claims 2
SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 claims 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
229910000027 potassium carbonate Inorganic materials 0.000 claims 2
229910000160 potassium phosphate Inorganic materials 0.000 claims 2
235000011009 potassium phosphates Nutrition 0.000 claims 2
239000001488 sodium phosphate Substances 0.000 claims 2
229910000162 sodium phosphate Inorganic materials 0.000 claims 2
150000003512 tertiary amines Chemical class 0.000 claims 2
SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 claims 2
125000003944 tolyl group Chemical group 0.000 claims 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims 2
CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 claims 2
MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 claims 1
WIHHVKUARKTSBU-UHFFFAOYSA-N 4-bromobenzene-1,2-diamine Chemical compound NC1=CC=C(Br)C=C1N WIHHVKUARKTSBU-UHFFFAOYSA-N 0.000 claims 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
239000005695 Ammonium acetate Substances 0.000 claims 1
239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
NEORDKUCAJWSBS-UHFFFAOYSA-L [K+].[K+].OC([O-])=O.OP(O)([O-])=O Chemical group [K+].[K+].OC([O-])=O.OP(O)([O-])=O NEORDKUCAJWSBS-UHFFFAOYSA-L 0.000 claims 1
235000019257 ammonium acetate Nutrition 0.000 claims 1
229940043376 ammonium acetate Drugs 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
239000007822 coupling agent Substances 0.000 claims 1
JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical group [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 claims 1
ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical group B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 claims 1
235000019253 formic acid Nutrition 0.000 claims 1
150000004674 formic acids Chemical class 0.000 claims 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
-1 neopentyl glycolate Chemical compound 0.000 claims 1
239000012454 non-polar solvent Substances 0.000 claims 1
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims 1
239000003880 polar aprotic solvent Substances 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
235000011181 potassium carbonates Nutrition 0.000 claims 1
235000017550 sodium carbonate Nutrition 0.000 claims 1

Classifications

- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- 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
- C07D403/14—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 three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

RU2018107689A 2015-08-03 2016-07-28 Способ синтеза равидасвира RU2018107689A (ru)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ITUB2015A002784A ITUB20152784A1 (it)	2015-08-03	2015-08-03	Processo per la sintesi di ravidasvir
ITUB2015A002784		2015-08-03
PCT/EP2016/068019 WO2017021270A1 (en)	2015-08-03	2016-07-28	Process for the synthesis of ravidasvir

Publications (2)

Publication Number	Publication Date
RU2018107689A true RU2018107689A (ru)	2019-09-05
RU2018107689A3 RU2018107689A3 (es)	2019-12-24

Family

ID=54364584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
RU2018107689A RU2018107689A (ru)	2015-08-03	2016-07-28	Способ синтеза равидасвира

Country Status (6)

Country	Link
EP (1)	EP3331874A1 (es)
CN (1)	CN108349950A (es)
IT (1)	ITUB20152784A1 (es)
MX (1)	MX2018001296A (es)
RU (1)	RU2018107689A (es)
WO (1)	WO2017021270A1 (es)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011091446A1 (en) *	2010-01-22	2011-07-28	Glaxosmithkline Llc	Chemical compounds
US8877707B2 (en) *	2010-05-24	2014-11-04	Presidio Pharmaceuticals, Inc.	Inhibitors of HCV NS5A
WO2013123092A1 (en) *	2012-02-13	2013-08-22	Presidio Pharmaceuticals, Inc.	Solid forms comprising inhibitors of hcv ns5a, compositions thereof, and uses therewith

2015
- 2015-08-03 IT ITUB2015A002784A patent/ITUB20152784A1/it unknown
2016
- 2016-07-28 CN CN201680051952.3A patent/CN108349950A/zh active Pending
- 2016-07-28 WO PCT/EP2016/068019 patent/WO2017021270A1/en not_active Ceased
- 2016-07-28 MX MX2018001296A patent/MX2018001296A/es unknown
- 2016-07-28 EP EP16745696.1A patent/EP3331874A1/en not_active Withdrawn
- 2016-07-28 RU RU2018107689A patent/RU2018107689A/ru not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO2017021270A1 (en)	2017-02-09
CN108349950A (zh)	2018-07-31
ITUB20152784A1 (it)	2017-02-03
RU2018107689A3 (es)	2019-12-24
EP3331874A1 (en)	2018-06-13
MX2018001296A (es)	2018-05-22

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Legal Events

Date	Code	Title	Description
2020-04-27	FA92	Acknowledgement of application withdrawn (lack of supplementary materials submitted)	Effective date: 20200423