ES2671732T3 - Procedimiento mejorado para preparar un compuesto intermedio del inhibidor de proteasa macrocíclico TMC 435 - Google Patents
Procedimiento mejorado para preparar un compuesto intermedio del inhibidor de proteasa macrocíclico TMC 435 Download PDFInfo
- Publication number
- ES2671732T3 ES2671732T3 ES12790677.4T ES12790677T ES2671732T3 ES 2671732 T3 ES2671732 T3 ES 2671732T3 ES 12790677 T ES12790677 T ES 12790677T ES 2671732 T3 ES2671732 T3 ES 2671732T3
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- Prior art keywords
- alpha
- adrenergic receptor
- present
- pharmaceutically acceptable
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 1
- 229940055577 oleyl alcohol Drugs 0.000 claims 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 1
- 229940014662 pantothenate Drugs 0.000 claims 1
- 235000019161 pantothenic acid Nutrition 0.000 claims 1
- 239000011713 pantothenic acid Substances 0.000 claims 1
- 229940119519 peg-32 stearate Drugs 0.000 claims 1
- 229940119517 peg-6 stearate Drugs 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims 1
- 229960003415 propylparaben Drugs 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 238000007665 sagging Methods 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
- 229960001860 salicylate Drugs 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000004408 titanium dioxide Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 229940042129 topical gel Drugs 0.000 claims 1
- 150000003626 triacylglycerols Chemical class 0.000 claims 1
- 230000037303 wrinkles Effects 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 11
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract description 7
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 4
- 150000003855 acyl compounds Chemical class 0.000 abstract description 4
- 125000002252 acyl group Chemical group 0.000 abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000003963 dichloro group Chemical group Cl* 0.000 description 7
- RUKVGXGTVPPWDD-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)imidazolidine Chemical group CC1=CC(C)=CC(C)=C1N1CN(C=2C(=CC(C)=CC=2C)C)CC1 RUKVGXGTVPPWDD-UHFFFAOYSA-N 0.000 description 4
- 238000005649 metathesis reaction Methods 0.000 description 4
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 4
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 4
- GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 4
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- GHPHCACQRYSXSS-UHFFFAOYSA-N ruthenium;tricyclohexylphosphane Chemical compound [Ru].C1CCCCC1P(C1CCCCC1)C1CCCCC1 GHPHCACQRYSXSS-UHFFFAOYSA-N 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 125000006684 polyhaloalkyl group Polymers 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- CVRYHAXYVVFEDI-UHFFFAOYSA-N [Ru].ClP(C(P(C1CCCCC1)(C1CCCCC1)(C1CCCCC1)Cl)C1=CC=CC=C1)(C1CCCCC1)(C1CCCCC1)C1CCCCC1 Chemical compound [Ru].ClP(C(P(C1CCCCC1)(C1CCCCC1)(C1CCCCC1)Cl)C1=CC=CC=C1)(C1CCCCC1)(C1CCCCC1)C1CCCCC1 CVRYHAXYVVFEDI-UHFFFAOYSA-N 0.000 description 1
- FCDPQMAOJARMTG-UHFFFAOYSA-L benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium;tricyclohexylphosphane Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1.CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=[Ru](Cl)(Cl)=CC1=CC=CC=C1 FCDPQMAOJARMTG-UHFFFAOYSA-L 0.000 description 1
- UDWHYAPPVOEOMP-UHFFFAOYSA-L dichloro(phenylsulfanylmethylidene)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CSC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 UDWHYAPPVOEOMP-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- WYXALVMTSDYYSL-UHFFFAOYSA-N ruthenium;tricyclohexylphosphane Chemical compound [Ru].C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 WYXALVMTSDYYSL-UHFFFAOYSA-N 0.000 description 1
- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- 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
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11187025 | 2011-10-28 | ||
| EP11187025 | 2011-10-28 | ||
| PCT/IB2012/055900 WO2013061285A1 (en) | 2011-10-28 | 2012-10-26 | Improved process for preparing an intermediate of the macrocyclic protease inhibitor tmc 435 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2671732T3 true ES2671732T3 (es) | 2018-06-08 |
Family
ID=47221505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12790677.4T Active ES2671732T3 (es) | 2011-10-28 | 2012-10-26 | Procedimiento mejorado para preparar un compuesto intermedio del inhibidor de proteasa macrocíclico TMC 435 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US8981082B2 (enExample) |
| EP (1) | EP2771339B1 (enExample) |
| JP (1) | JP6231482B2 (enExample) |
| KR (1) | KR20140086967A (enExample) |
| CN (1) | CN104053658B (enExample) |
| AR (1) | AR088568A1 (enExample) |
| AU (1) | AU2012327934B2 (enExample) |
| BR (1) | BR112014009849A2 (enExample) |
| CA (1) | CA2848377A1 (enExample) |
| CL (1) | CL2014001043A1 (enExample) |
| EA (1) | EA201490892A1 (enExample) |
| ES (1) | ES2671732T3 (enExample) |
| HK (1) | HK1202120A1 (enExample) |
| IL (1) | IL231892A (enExample) |
| MX (1) | MX347650B (enExample) |
| TW (1) | TWI574960B (enExample) |
| WO (1) | WO2013061285A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA41812A (fr) | 2015-03-27 | 2018-01-30 | Janssen Pharmaceuticals Inc | Procédés et intermédiaires pour la préparation d'un inhibiteur de protéase macrocyclique du vhc |
| WO2017064680A1 (en) * | 2015-10-16 | 2017-04-20 | Lupin Limited | An improved process for the preparation of simeprevir sodium and intermediate thereof |
| CN109846883A (zh) * | 2017-11-30 | 2019-06-07 | 常州寅盛药业有限公司 | 苯并呋喃衍生物与tmc435联合用药物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007523833A (ja) | 2003-04-10 | 2007-08-23 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ルテニウム錯体触媒メタセシス反応による大環状化合物の製造方法 |
| PE20070211A1 (es) * | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| WO2007030656A1 (en) * | 2005-09-09 | 2007-03-15 | Boehringer Ingelheim International Gmbh | Ring-closing metathesis process for the preparation of macrocyclic peptides |
| US8193346B2 (en) | 2007-12-06 | 2012-06-05 | Enanta Pharmaceuticals, Inc. | Process for making macrocyclic oximyl hepatitis C protease inhibitors |
| CA2732091A1 (en) * | 2008-08-07 | 2010-02-11 | F. Hoffmann-La Roche Ag | Process for the preparation of a macrocycle |
| MX2011006764A (es) | 2008-12-23 | 2011-08-03 | Ortho Mcneil Janssen Pharm | Procedimiento y compuestos intermedios para preparar un inhibidor de proteasa macrociclico del vhc. |
-
2012
- 2012-10-26 JP JP2014537794A patent/JP6231482B2/ja not_active Expired - Fee Related
- 2012-10-26 CA CA2848377A patent/CA2848377A1/en not_active Abandoned
- 2012-10-26 CN CN201280052692.3A patent/CN104053658B/zh not_active Expired - Fee Related
- 2012-10-26 HK HK15102687.7A patent/HK1202120A1/xx unknown
- 2012-10-26 AU AU2012327934A patent/AU2012327934B2/en not_active Ceased
- 2012-10-26 EA EA201490892A patent/EA201490892A1/ru unknown
- 2012-10-26 BR BR112014009849A patent/BR112014009849A2/pt not_active IP Right Cessation
- 2012-10-26 KR KR1020147009887A patent/KR20140086967A/ko not_active Ceased
- 2012-10-26 EP EP12790677.4A patent/EP2771339B1/en active Active
- 2012-10-26 TW TW101139616A patent/TWI574960B/zh not_active IP Right Cessation
- 2012-10-26 US US14/350,138 patent/US8981082B2/en not_active Expired - Fee Related
- 2012-10-26 MX MX2014005070A patent/MX347650B/es active IP Right Grant
- 2012-10-26 AR ARP120104040A patent/AR088568A1/es unknown
- 2012-10-26 ES ES12790677.4T patent/ES2671732T3/es active Active
- 2012-10-26 WO PCT/IB2012/055900 patent/WO2013061285A1/en not_active Ceased
-
2014
- 2014-04-03 IL IL231892A patent/IL231892A/en not_active IP Right Cessation
- 2014-04-24 CL CL2014001043A patent/CL2014001043A1/es unknown
-
2015
- 2015-02-09 US US14/616,770 patent/US9328108B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN104053658B (zh) | 2018-03-13 |
| CL2014001043A1 (es) | 2014-07-25 |
| TWI574960B (zh) | 2017-03-21 |
| US9328108B2 (en) | 2016-05-03 |
| US20140235852A1 (en) | 2014-08-21 |
| TW201323423A (zh) | 2013-06-16 |
| MX347650B (es) | 2017-05-05 |
| CA2848377A1 (en) | 2013-05-02 |
| MX2014005070A (es) | 2014-08-22 |
| AU2012327934A1 (en) | 2014-03-20 |
| EP2771339A1 (en) | 2014-09-03 |
| US20150152098A1 (en) | 2015-06-04 |
| IL231892A (en) | 2017-09-28 |
| KR20140086967A (ko) | 2014-07-08 |
| AU2012327934B2 (en) | 2017-06-01 |
| JP2014530901A (ja) | 2014-11-20 |
| BR112014009849A2 (pt) | 2016-07-05 |
| HK1202120A1 (en) | 2015-09-18 |
| JP6231482B2 (ja) | 2017-11-15 |
| CN104053658A (zh) | 2014-09-17 |
| EP2771339B1 (en) | 2018-04-18 |
| WO2013061285A1 (en) | 2013-05-02 |
| AR088568A1 (es) | 2014-06-18 |
| EA201490892A1 (ru) | 2014-08-29 |
| US8981082B2 (en) | 2015-03-17 |
| IL231892A0 (en) | 2014-05-28 |
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