CA2485739A1 - Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanone - Google Patents
Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanoneInfo
- Publication number
- CA2485739A1 CA2485739A1 CA002485739A CA2485739A CA2485739A1 CA 2485739 A1 CA2485739 A1 CA 2485739A1 CA 002485739 A CA002485739 A CA 002485739A CA 2485739 A CA2485739 A CA 2485739A CA 2485739 A1 CA2485739 A1 CA 2485739A1
- Authority
- CA
- Canada
- Prior art keywords
- methylpyridin
- ethanone
- phenyl
- preparing
- methylsulphonyl
- Prior art date
- 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.)
- Granted
Links
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- -1 6-Methylpyridin-3-yl Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940111134 coxibs Drugs 0.000 abstract 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
Abstract
1- (6-Methylpyridin-3-yl) -2- [ (4- (methylsulfonyl)phenyl] ethanone of the formula <See formula I> and a process for preparing such is disclosed. 1-(6-Methylpyridin-3-yl) -2- [(4-(methylsulfonyl)phenyl] ethanone is an important intermediate for preparing so-called COX-2 inhibitors, which are pharmaceutically active compounds having analgesic and anti-inflammatory action.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH99100590.1 | 1999-01-14 | ||
EP99100590 | 1999-01-14 | ||
US14599699P | 1999-07-29 | 1999-07-29 | |
US60/145,996 | 1999-07-29 | ||
CA002359958A CA2359958C (en) | 1999-01-14 | 2000-01-13 | Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002359958A Division CA2359958C (en) | 1999-01-14 | 2000-01-13 | Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2485739A1 true CA2485739A1 (en) | 2000-07-20 |
CA2485739C CA2485739C (en) | 2009-09-22 |
Family
ID=34089809
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002485739A Expired - Fee Related CA2485739C (en) | 1999-01-14 | 2000-01-13 | Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanone |
CA002359958A Expired - Fee Related CA2359958C (en) | 1999-01-14 | 2000-01-13 | Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002359958A Expired - Fee Related CA2359958C (en) | 1999-01-14 | 2000-01-13 | Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone |
Country Status (15)
Country | Link |
---|---|
EP (2) | EP1394149B1 (en) |
JP (1) | JP4765167B2 (en) |
CN (2) | CN1170820C (en) |
AT (2) | ATE287396T1 (en) |
AU (1) | AU2290800A (en) |
CA (2) | CA2485739C (en) |
CZ (1) | CZ302270B6 (en) |
DE (2) | DE50009312D1 (en) |
DK (2) | DK1394149T3 (en) |
ES (2) | ES2235138T3 (en) |
HU (1) | HUP0105124A3 (en) |
IL (1) | IL143981A0 (en) |
PT (2) | PT1394149E (en) |
SK (1) | SK284903B6 (en) |
WO (1) | WO2000042014A2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104725300A (en) * | 2015-02-28 | 2015-06-24 | 宁波九胜创新医药科技有限公司 | Preparation method of 1-(6-methyl pyridine-3-yl)-2-(4-methylsulfonyl phenyl) ethanone |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3313683A (en) * | 1963-04-22 | 1967-04-11 | Lilly Co Eli | Nematocidal and fungicidal methods |
FR2074674A1 (en) * | 1970-01-16 | 1971-10-08 | Simafex | Sulphonamide/aldehyde-bisulphite complexes - antibacterials with very high solubility in water |
US4155909A (en) * | 1977-06-13 | 1979-05-22 | Philip Morris Incorporated | 2-Alkyl nicotinoids and processes for their production |
US5596008A (en) * | 1995-02-10 | 1997-01-21 | G. D. Searle & Co. | 3,4-Diaryl substituted pyridines for the treatment of inflammation |
BRPI9710372B8 (en) * | 1996-07-18 | 2021-05-25 | Merck Canada Inc | compound, and, pharmaceutical composition. |
TW492959B (en) * | 1997-04-18 | 2002-07-01 | Merck & Co Inc | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
AR015938A1 (en) * | 1997-09-25 | 2001-05-30 | Merck Sharp & Dohme | PROCEDURE TO PREPARE DIARIL PIRIDINES USEFUL AS COX-2 INHIBITORS AND INTERMEDIATE COMPOUND |
PT1071745E (en) * | 1998-04-24 | 2004-11-30 | Merck & Co Inc | PROCESS FOR SYNTHESIZING COX-2 INHIBITORS |
-
2000
- 2000-01-13 HU HU0105124A patent/HUP0105124A3/en unknown
- 2000-01-13 CN CNB008027218A patent/CN1170820C/en not_active Expired - Fee Related
- 2000-01-13 ES ES03024787T patent/ES2235138T3/en not_active Expired - Lifetime
- 2000-01-13 EP EP03024787A patent/EP1394149B1/en not_active Expired - Lifetime
- 2000-01-13 CZ CZ20012457A patent/CZ302270B6/en not_active IP Right Cessation
- 2000-01-13 JP JP2000593582A patent/JP4765167B2/en not_active Expired - Fee Related
- 2000-01-13 DE DE50009312T patent/DE50009312D1/en not_active Expired - Lifetime
- 2000-01-13 CA CA002485739A patent/CA2485739C/en not_active Expired - Fee Related
- 2000-01-13 PT PT03024787T patent/PT1394149E/en unknown
- 2000-01-13 WO PCT/EP2000/000240 patent/WO2000042014A2/en active Application Filing
- 2000-01-13 IL IL14398100A patent/IL143981A0/en active IP Right Grant
- 2000-01-13 ES ES00901555T patent/ES2209807T3/en not_active Expired - Lifetime
- 2000-01-13 PT PT00901555T patent/PT1159270E/en unknown
- 2000-01-13 SK SK972-2001A patent/SK284903B6/en not_active IP Right Cessation
- 2000-01-13 EP EP00901555A patent/EP1159270B1/en not_active Expired - Lifetime
- 2000-01-13 CN CNB200410069946XA patent/CN1281589C/en not_active Expired - Fee Related
- 2000-01-13 DE DE50004327T patent/DE50004327D1/en not_active Expired - Lifetime
- 2000-01-13 AT AT03024787T patent/ATE287396T1/en active
- 2000-01-13 CA CA002359958A patent/CA2359958C/en not_active Expired - Fee Related
- 2000-01-13 DK DK03024787T patent/DK1394149T3/en active
- 2000-01-13 DK DK00901555T patent/DK1159270T3/en active
- 2000-01-13 AT AT00901555T patent/ATE253559T1/en active
- 2000-01-13 AU AU22908/00A patent/AU2290800A/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP1394149B1 (en) | 2005-01-19 |
EP1159270A2 (en) | 2001-12-05 |
PT1394149E (en) | 2005-05-31 |
DE50004327D1 (en) | 2003-12-11 |
DK1159270T3 (en) | 2004-02-23 |
CN1281589C (en) | 2006-10-25 |
SK9722001A3 (en) | 2001-12-03 |
CZ302270B6 (en) | 2011-01-19 |
WO2000042014A2 (en) | 2000-07-20 |
DE50009312D1 (en) | 2005-02-24 |
JP2003518002A (en) | 2003-06-03 |
ATE287396T1 (en) | 2005-02-15 |
CN1583723A (en) | 2005-02-23 |
EP1159270B1 (en) | 2003-11-05 |
ATE253559T1 (en) | 2003-11-15 |
CZ20012457A3 (en) | 2002-01-16 |
HUP0105124A2 (en) | 2002-04-29 |
IL143981A0 (en) | 2002-04-21 |
ES2209807T3 (en) | 2004-07-01 |
CA2359958C (en) | 2006-04-04 |
CA2359958A1 (en) | 2000-07-20 |
CN1170820C (en) | 2004-10-13 |
ES2235138T3 (en) | 2005-07-01 |
DK1394149T3 (en) | 2005-04-04 |
CN1359374A (en) | 2002-07-17 |
HUP0105124A3 (en) | 2002-05-28 |
CA2485739C (en) | 2009-09-22 |
AU2290800A (en) | 2000-08-01 |
JP4765167B2 (en) | 2011-09-07 |
EP1394149A1 (en) | 2004-03-03 |
WO2000042014A3 (en) | 2000-12-07 |
SK284903B6 (en) | 2006-02-02 |
PT1159270E (en) | 2004-03-31 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDC | Discontinued application reinstated | ||
MKLA | Lapsed |
Effective date: 20130114 |