HUP0003155A2 - Eljárás COX-2 inhibitorként alkalmazható 2-aril-3-aril-5-halogénpiridin-származékok előállítására - Google Patents
Eljárás COX-2 inhibitorként alkalmazható 2-aril-3-aril-5-halogénpiridin-származékok előállításáraInfo
- Publication number
- HUP0003155A2 HUP0003155A2 HU0003155A HUP0003155A HUP0003155A2 HU P0003155 A2 HUP0003155 A2 HU P0003155A2 HU 0003155 A HU0003155 A HU 0003155A HU P0003155 A HUP0003155 A HU P0003155A HU P0003155 A2 HUP0003155 A2 HU P0003155A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- aryl
- inhibitors
- carbon atoms
- cox
- Prior art date
Links
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title abstract 3
- 229940111134 coxibs Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000001475 halogen functional group Chemical group 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- -1 trifluoromethylcarbonylamino group Chemical group 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
- C07D213/60—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 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
-
- 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
- C07D213/52—Sulfur atoms
-
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
A találmány eljárás COX-2 inhibitorokként hasznosítható 2-aril-3-aril-5-halogénpiridin-származékok előállítására. Közelebbről a találmány akövetkezőkben ismertetésre kerülő (I) általános képletű vegyületekelőállítására vonatkozik, mely vegyületek potens ciklooxigenáz-2-inhibitorok, ezáltal elsősorban gyulladásgátló hatóanyagokkénthasznosíthatók. Az (I) általános képleben R1 jelentése (a) metilcsoport, (b) aminocsoport, (c)trifluormetilkarbonilaminocsoport vagy (d) metilaminocsoport; Arjelentése mono-, di- vagy triszubsztituált fenil- vagypiridinilcsoport (vagy az utóbbi N-oxidja), mimellett aszubsztituensek a következők lehetnek: (a) hidrogénatom, (b)halogénatom, (c) 1-4 szénatomot tartalmazó alkoxicsoport, (d) 1-4szénatomot tartalmazó alkiltiocsoport, (e) cianocsoport, (f) 1-4szénatomot tartalmazó alkilcsoport és (g) 1-4 szénatomot tartalmazó fluoralkilcsoport; R2 jelentése (a)fluor-, klór-, bróm vagy jódatom, (b) cianocsoport vagy (c)azidocsoport. Ó
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4564297P | 1997-04-18 | 1997-04-18 | |
| GBGB9709686.1A GB9709686D0 (en) | 1997-05-13 | 1997-05-13 | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
| PCT/US1998/008312 WO1998047871A1 (en) | 1997-04-18 | 1998-04-14 | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP0003155A2 true HUP0003155A2 (hu) | 2001-06-28 |
| HUP0003155A3 HUP0003155A3 (en) | 2002-01-28 |
| HU226999B1 HU226999B1 (en) | 2010-04-28 |
Family
ID=26311530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0003155A HU226999B1 (en) | 1997-04-18 | 1998-04-14 | Process for making 2,3-diarylpyridines useful as cox-2 inhibitors, and intermediates |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0975596B1 (hu) |
| JP (1) | JP3300369B2 (hu) |
| KR (1) | KR20010006546A (hu) |
| CN (1) | CN1182117C (hu) |
| AT (1) | ATE270275T1 (hu) |
| AU (1) | AU729730B2 (hu) |
| BR (1) | BR9808923B1 (hu) |
| CA (1) | CA2287482C (hu) |
| CZ (1) | CZ293246B6 (hu) |
| DE (1) | DE69824839T2 (hu) |
| EA (1) | EA002190B1 (hu) |
| ES (1) | ES2223128T3 (hu) |
| HK (1) | HK1023771A1 (hu) |
| HR (1) | HRP980206B1 (hu) |
| HU (1) | HU226999B1 (hu) |
| NZ (1) | NZ500390A (hu) |
| PL (1) | PL190265B1 (hu) |
| RS (1) | RS49901B (hu) |
| SK (1) | SK285037B6 (hu) |
| TW (1) | TW492959B (hu) |
| UA (1) | UA66792C2 (hu) |
| WO (1) | WO1998047871A1 (hu) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000042014A2 (de) * | 1999-01-14 | 2000-07-20 | Lonza Ag | 1-(6-methylpyridin-3-yl)-2-((4-(methylsulfonyl)phenyl)ethanon und verfahren zu seiner herstellung |
| KR100446324B1 (ko) * | 1999-01-14 | 2004-08-30 | 론자 아게 | 1-(6-메틸피리딘-3-일)-2-[4-(메틸술포닐)페닐]에타논 및이의 제조 방법 |
| WO2001007410A1 (en) * | 1999-07-27 | 2001-02-01 | Lonza Ag | Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl) phenyl] ethanone |
| US6566527B1 (en) | 1999-07-27 | 2003-05-20 | Merck & Co., Inc. | Process for preparing 1-(6-methylpyridin-3-yl)-2-[4-methylsulphonyl)-phenyl]ethanone |
| EP1246621A4 (en) | 1999-12-23 | 2004-11-24 | Nitromed Inc | NITROSED AND NITROSYLATED CYCLOOXYGENASE-2 INHIBITORS, COMPOSITIONS AND METHODS FOR THEIR USE |
| JP2001261647A (ja) * | 2000-03-22 | 2001-09-26 | Sankio Chemical Co Ltd | ピリジン誘導体の製造方法 |
| PT1303265E (pt) | 2000-07-20 | 2007-10-09 | Lauras As | ''utilização de inibidores da cox-2 como imuno-estimulantes, no tratamento do vih ou da sida'' |
| EP2582690B1 (en) * | 2010-06-16 | 2018-07-25 | Glenmark Generics Limited | Process for preparation of 2, 3-diaryl-5-substituted pyridines and their intermediates |
| CA2817939A1 (en) * | 2010-11-15 | 2012-05-24 | Virdev Intermediates Pvt. Ltd. | A process for cyclooxygenase-2 selective inhibitor |
| CN103204803A (zh) | 2012-01-13 | 2013-07-17 | 阿尔弗雷德·E·蒂芬巴赫尔有限责任两合公司 | 用于合成依托考昔的方法 |
| WO2014114352A1 (en) * | 2013-01-25 | 2014-07-31 | Synthon Bv | Process for making etoricoxib |
| WO2015036550A1 (en) | 2013-09-13 | 2015-03-19 | Synthon B.V. | Process for making etoricoxib |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH561717A5 (hu) * | 1971-05-10 | 1975-05-15 | Ciba Geigy Ag | |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5686470A (en) * | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
| RU2200158C2 (ru) * | 1995-02-13 | 2003-03-10 | Джи.Ди.Сирл энд Ко. | Замещенные изоксазолы, фармацевтические композиции на их основе и способ подавления воспалений |
| US5643933A (en) * | 1995-06-02 | 1997-07-01 | G. D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
| US5677318A (en) * | 1996-07-11 | 1997-10-14 | Merck Frosst Canada, Inc. | Diphenyl-1,2-3-thiadiazoles as anti-inflammatory agents |
| SK283261B6 (sk) * | 1996-07-18 | 2003-04-01 | Merck Frosst Canada & Co. / Merck Frosst Canada & Cie. | Substituované pyridíny, farmaceutický prostriedok s ich obsahom a ich použitie |
-
1998
- 1998-04-09 TW TW087105349A patent/TW492959B/zh not_active IP Right Cessation
- 1998-04-14 WO PCT/US1998/008312 patent/WO1998047871A1/en active IP Right Grant
- 1998-04-14 PL PL98336298A patent/PL190265B1/pl not_active IP Right Cessation
- 1998-04-14 SK SK1436-99A patent/SK285037B6/sk not_active IP Right Cessation
- 1998-04-14 BR BRPI9808923-4A patent/BR9808923B1/pt not_active IP Right Cessation
- 1998-04-14 CZ CZ19993690A patent/CZ293246B6/cs not_active IP Right Cessation
- 1998-04-14 DE DE69824839T patent/DE69824839T2/de not_active Expired - Lifetime
- 1998-04-14 AT AT98919881T patent/ATE270275T1/de not_active IP Right Cessation
- 1998-04-14 KR KR1019997009636A patent/KR20010006546A/ko not_active IP Right Cessation
- 1998-04-14 EP EP98919881A patent/EP0975596B1/en not_active Expired - Lifetime
- 1998-04-14 NZ NZ500390A patent/NZ500390A/en unknown
- 1998-04-14 CN CNB988061864A patent/CN1182117C/zh not_active Expired - Fee Related
- 1998-04-14 CA CA002287482A patent/CA2287482C/en not_active Expired - Fee Related
- 1998-04-14 HU HU0003155A patent/HU226999B1/hu not_active IP Right Cessation
- 1998-04-14 RS YUP-536/99A patent/RS49901B/sr unknown
- 1998-04-14 AU AU72571/98A patent/AU729730B2/en not_active Ceased
- 1998-04-14 JP JP54636798A patent/JP3300369B2/ja not_active Expired - Fee Related
- 1998-04-14 ES ES98919881T patent/ES2223128T3/es not_active Expired - Lifetime
- 1998-04-14 UA UA99116266A patent/UA66792C2/uk unknown
- 1998-04-14 EA EA199900948A patent/EA002190B1/ru not_active IP Right Cessation
- 1998-04-16 HR HR980206A patent/HRP980206B1/xx not_active IP Right Cessation
-
2000
- 2000-05-16 HK HK00102924A patent/HK1023771A1/xx not_active IP Right Cessation
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