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)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (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 (https=) |
| EP (1) | EP2771339B1 (https=) |
| JP (1) | JP6231482B2 (https=) |
| KR (1) | KR20140086967A (https=) |
| CN (1) | CN104053658B (https=) |
| AR (1) | AR088568A1 (https=) |
| AU (1) | AU2012327934B2 (https=) |
| BR (1) | BR112014009849A2 (https=) |
| CA (1) | CA2848377A1 (https=) |
| CL (1) | CL2014001043A1 (https=) |
| EA (1) | EA201490892A1 (https=) |
| ES (1) | ES2671732T3 (https=) |
| HK (1) | HK1202120A1 (https=) |
| IL (1) | IL231892A (https=) |
| MX (1) | MX347650B (https=) |
| TW (1) | TWI574960B (https=) |
| WO (1) | WO2013061285A1 (https=) |
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 |
|---|---|---|---|---|
| CA2521835A1 (en) * | 2003-04-10 | 2004-10-21 | Boehringer Ingelheim International Gmbh | Process for the preparation of macrocyclic compounds by ruthenium complex catalysed metathesis reaction |
| PE20070211A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| EP1934243B1 (en) | 2005-09-09 | 2011-05-25 | 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 |
| KR101647520B1 (ko) | 2008-08-07 | 2016-08-10 | 에프. 호프만-라 로슈 아게 | 거대환식 화합물의 제조 방법 |
| JP5687631B2 (ja) * | 2008-12-23 | 2015-03-18 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツドＪａｎｓｓｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ． | Ｈｃｖのマクロ環状プロテアーゼ阻害剤を製造するための方法および中間体 |
-
2012
- 2012-10-26 TW TW101139616A patent/TWI574960B/zh not_active IP Right Cessation
- 2012-10-26 WO PCT/IB2012/055900 patent/WO2013061285A1/en not_active Ceased
- 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 MX MX2014005070A patent/MX347650B/es active IP Right Grant
- 2012-10-26 AR ARP120104040A patent/AR088568A1/es unknown
- 2012-10-26 AU AU2012327934A patent/AU2012327934B2/en not_active Ceased
- 2012-10-26 US US14/350,138 patent/US8981082B2/en not_active Expired - Fee Related
- 2012-10-26 ES ES12790677.4T patent/ES2671732T3/es active Active
- 2012-10-26 HK HK15102687.7A patent/HK1202120A1/xx unknown
- 2012-10-26 JP JP2014537794A patent/JP6231482B2/ja not_active Expired - Fee Related
- 2012-10-26 EP EP12790677.4A patent/EP2771339B1/en active Active
- 2012-10-26 CN CN201280052692.3A patent/CN104053658B/zh not_active Expired - Fee Related
- 2012-10-26 EA EA201490892A patent/EA201490892A1/ru unknown
- 2012-10-26 CA CA2848377A patent/CA2848377A1/en not_active Abandoned
-
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 |
|---|---|
| AU2012327934B2 (en) | 2017-06-01 |
| AU2012327934A1 (en) | 2014-03-20 |
| KR20140086967A (ko) | 2014-07-08 |
| HK1202120A1 (en) | 2015-09-18 |
| CL2014001043A1 (es) | 2014-07-25 |
| JP6231482B2 (ja) | 2017-11-15 |
| CN104053658B (zh) | 2018-03-13 |
| BR112014009849A2 (pt) | 2016-07-05 |
| US8981082B2 (en) | 2015-03-17 |
| CN104053658A (zh) | 2014-09-17 |
| JP2014530901A (ja) | 2014-11-20 |
| EP2771339B1 (en) | 2018-04-18 |
| WO2013061285A1 (en) | 2013-05-02 |
| US20140235852A1 (en) | 2014-08-21 |
| MX2014005070A (es) | 2014-08-22 |
| MX347650B (es) | 2017-05-05 |
| EP2771339A1 (en) | 2014-09-03 |
| CA2848377A1 (en) | 2013-05-02 |
| AR088568A1 (es) | 2014-06-18 |
| TW201323423A (zh) | 2013-06-16 |
| US20150152098A1 (en) | 2015-06-04 |
| IL231892A0 (en) | 2014-05-28 |
| IL231892A (en) | 2017-09-28 |
| EA201490892A1 (ru) | 2014-08-29 |
| US9328108B2 (en) | 2016-05-03 |
| TWI574960B (zh) | 2017-03-21 |
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