ZA200200504B - Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates. - Google Patents
Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates. Download PDFInfo
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- ZA200200504B ZA200200504B ZA200200504A ZA200200504A ZA200200504B ZA 200200504 B ZA200200504 B ZA 200200504B ZA 200200504 A ZA200200504 A ZA 200200504A ZA 200200504 A ZA200200504 A ZA 200200504A ZA 200200504 B ZA200200504 B ZA 200200504B
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- South Africa
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- cycloalkyl
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- 238000002360 preparation method Methods 0.000 title description 20
- 239000000543 intermediate Substances 0.000 title description 12
- 241000709661 Enterovirus Species 0.000 title description 5
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 159
- 238000000034 method Methods 0.000 claims description 77
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 230000008569 process Effects 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 239000011541 reaction mixture Substances 0.000 claims description 26
- -1 Boc group Chemical group 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 230000002194 synthesizing effect Effects 0.000 claims description 10
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
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- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/2435—Loop-type reactors
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2475—Membrane reactors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00099—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor the reactor being immersed in the heat exchange medium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Enzymes And Modification Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15035899P | 1999-08-24 | 1999-08-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200200504B true ZA200200504B (en) | 2003-03-26 |
Family
ID=22534156
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200200504A ZA200200504B (en) | 1999-08-24 | 2002-01-21 | Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates. |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP1206450A1 (cs) |
JP (1) | JP2003507453A (cs) |
KR (1) | KR20020046283A (cs) |
CN (1) | CN1168713C (cs) |
AR (1) | AR025380A1 (cs) |
AU (1) | AU770221B2 (cs) |
BR (1) | BR0013306A (cs) |
CA (1) | CA2376452A1 (cs) |
CO (1) | CO5200782A1 (cs) |
CZ (1) | CZ2002632A3 (cs) |
HK (1) | HK1049336B (cs) |
HU (1) | HUP0203365A3 (cs) |
IL (1) | IL147674A0 (cs) |
MX (1) | MXPA02001944A (cs) |
PE (1) | PE20010517A1 (cs) |
PL (1) | PL353997A1 (cs) |
TW (1) | TWI245040B (cs) |
UY (1) | UY26307A1 (cs) |
WO (1) | WO2001014329A1 (cs) |
ZA (1) | ZA200200504B (cs) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TR200003159T2 (tr) | 1998-04-30 | 2001-09-21 | Agouron Pharmaceuticals,Inc. | Antipicornaviral bileşikler, hazırlanışları ve kullanımları |
MXPA02001179A (es) | 1999-08-04 | 2002-07-30 | Agouron Pharma | Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y materiales para su sintesis. |
PE20020157A1 (es) | 1999-12-03 | 2002-02-22 | Agouron Pharma | Compuestos derivados de piridona como inhibidores de proteasas de picornaviral 3c, composiciones, sus usos farmaceuticos y materiales para su sintesis |
PE20011277A1 (es) | 2000-04-14 | 2002-01-07 | Agouron Pharma | Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis |
CN1525957A (zh) | 2000-06-14 | 2004-09-01 | ������ҩ������˾ | 抗细小核糖核酸病毒的化合物与组合物,它们的药物用途,以及用于其合成的物质 |
CN1309712C (zh) * | 2004-04-02 | 2007-04-11 | 中国科学院上海有机化学研究所 | Ag7088类化合物的关键中间体的前体及其合成方法 |
US20230157998A1 (en) | 2020-03-06 | 2023-05-25 | Pfizer Inc. | Methods of Inhibiting SARS-CoV-2 Replication and Treating Corona Virus Disease 2019 |
CN115322130B (zh) * | 2022-08-02 | 2024-05-14 | 南京正济医药研究有限公司 | 制备(s)-2-(boc-氨基)-3-[(s)-2-氧代-3-吡咯烷基]丙酸甲酯 |
CN115260074B (zh) * | 2022-08-02 | 2024-06-21 | 爱斯特(成都)生物制药股份有限公司 | 一种口服抗病毒药物Paxlovid中间体的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0910572B1 (en) * | 1996-05-14 | 2005-04-27 | Agouron Pharmaceuticals, Inc. | Inhibitors of picornavirus 3c proteases and methods for their use and preparation |
ATE248809T1 (de) * | 1997-03-28 | 2003-09-15 | Agouron Pharma | Gegen picorna-viren gerichtete verbindungen, zusammensetzungen die diese verbindungen enthalten und methoden zu ihrer anwendung |
US5962487A (en) * | 1997-12-16 | 1999-10-05 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds and methods for their use and preparation |
TR200003159T2 (tr) * | 1998-04-30 | 2001-09-21 | Agouron Pharmaceuticals,Inc. | Antipicornaviral bileşikler, hazırlanışları ve kullanımları |
-
2000
- 2000-08-22 PE PE2000000854A patent/PE20010517A1/es not_active Application Discontinuation
- 2000-08-23 CA CA002376452A patent/CA2376452A1/en not_active Abandoned
- 2000-08-23 HU HU0203365A patent/HUP0203365A3/hu unknown
- 2000-08-23 WO PCT/US2000/023033 patent/WO2001014329A1/en not_active Application Discontinuation
- 2000-08-23 CZ CZ2002632A patent/CZ2002632A3/cs unknown
- 2000-08-23 UY UY26307A patent/UY26307A1/es not_active Application Discontinuation
- 2000-08-23 EP EP00955831A patent/EP1206450A1/en not_active Withdrawn
- 2000-08-23 PL PL00353997A patent/PL353997A1/xx not_active Application Discontinuation
- 2000-08-23 KR KR1020027002322A patent/KR20020046283A/ko not_active Application Discontinuation
- 2000-08-23 CN CNB008118779A patent/CN1168713C/zh not_active Expired - Fee Related
- 2000-08-23 JP JP2001518419A patent/JP2003507453A/ja active Pending
- 2000-08-23 MX MXPA02001944A patent/MXPA02001944A/es active IP Right Grant
- 2000-08-23 IL IL14767400A patent/IL147674A0/xx unknown
- 2000-08-23 BR BR0013306-0A patent/BR0013306A/pt not_active IP Right Cessation
- 2000-08-23 AU AU67971/00A patent/AU770221B2/en not_active Ceased
- 2000-08-24 CO CO00063457A patent/CO5200782A1/es not_active Application Discontinuation
- 2000-08-24 AR ARP000104401A patent/AR025380A1/es unknown
- 2000-10-24 TW TW089117083A patent/TWI245040B/zh active
-
2002
- 2002-01-21 ZA ZA200200504A patent/ZA200200504B/en unknown
-
2003
- 2003-02-27 HK HK03101461.5A patent/HK1049336B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HK1049336A1 (en) | 2003-05-09 |
CN1374947A (zh) | 2002-10-16 |
AR025380A1 (es) | 2002-11-20 |
EP1206450A1 (en) | 2002-05-22 |
CA2376452A1 (en) | 2001-03-01 |
CZ2002632A3 (cs) | 2003-04-16 |
MXPA02001944A (es) | 2002-10-31 |
UY26307A1 (es) | 2001-04-30 |
JP2003507453A (ja) | 2003-02-25 |
HUP0203365A3 (en) | 2003-12-29 |
CN1168713C (zh) | 2004-09-29 |
BR0013306A (pt) | 2002-05-28 |
WO2001014329A1 (en) | 2001-03-01 |
TWI245040B (en) | 2005-12-11 |
IL147674A0 (en) | 2002-08-14 |
KR20020046283A (ko) | 2002-06-20 |
AU770221B2 (en) | 2004-02-19 |
HUP0203365A2 (hu) | 2003-02-28 |
HK1049336B (zh) | 2005-05-20 |
AU6797100A (en) | 2001-03-19 |
PE20010517A1 (es) | 2001-05-16 |
PL353997A1 (en) | 2003-12-15 |
CO5200782A1 (es) | 2002-09-27 |
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