UA73355C2 - 5-chlorine-3(4-methanesulfonylphenyl)-6'-methyl-[2,3']pyridinyl in pure crystallyne shape and a method for synthesis - Google Patents

5-chlorine-3(4-methanesulfonylphenyl)-6'-methyl-[2,3']pyridinyl in pure crystallyne shape and a method for synthesis Download PDF

Info

Publication number: UA73355C2
Authority: UA; Ukraine
Prior art keywords: compound; mixture; methanesulfonylphenyl; crystallyne; pyridinyl
Prior art date: 2000-05-26

Application number

UA20021210537A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Merck & Co Inc

Priority date (The priority date 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 date listed.)

2000-05-26

Filing date

2001-05-22

Publication date

2005-07-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22772880&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA73355(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-05-22 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

2005-07-15 Publication of UA73355C2 publication Critical patent/UA73355C2/uk

Links

238000000034 method Methods 0.000 title abstract description 13
230000015572 biosynthetic process Effects 0.000 title 1
125000004076 pyridyl group Chemical group 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
229940126062 Compound A Drugs 0.000 abstract description 18
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract description 18
201000010099 disease Diseases 0.000 abstract description 4
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239000008194 pharmaceutical composition Substances 0.000 abstract 1
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
238000012986 modification Methods 0.000 description 18
230000004048 modification Effects 0.000 description 18
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
239000000203 mixture Substances 0.000 description 13
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 5
239000012265 solid product Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000000113 differential scanning calorimetry Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
101000603223 Homo sapiens Nischarin Proteins 0.000 description 2
102100038995 Nischarin Human genes 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002129 infrared reflectance spectroscopy Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
229940011051 isopropyl acetate Drugs 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
201000008482 osteoarthritis Diseases 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
238000001291 vacuum drying Methods 0.000 description 2
SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
206010006811 Bursitis Diseases 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
108010037464 Cyclooxygenase 1 Proteins 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
241000110847 Kochia Species 0.000 description 1
241001275944 Misgurnus anguillicaudatus Species 0.000 description 1
201000002481 Myositis Diseases 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 1
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 1
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
208000036071 Rhinorrhea Diseases 0.000 description 1
206010039101 Rhinorrhoea Diseases 0.000 description 1
241000750042 Vini Species 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
239000013543 active substance Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical group C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
208000014674 injury Diseases 0.000 description 1
210000003041 ligament Anatomy 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000000634 powder X-ray diffraction Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
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239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
201000004595 synovitis Diseases 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
208000004371 toothache Diseases 0.000 description 1
230000008733 trauma Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 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
- 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
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UA20021210537A 2000-05-26 2001-05-22 5-chlorine-3(4-methanesulfonylphenyl)-6'-methyl-[2,3']pyridinyl in pure crystallyne shape and a method for synthesis UA73355C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US20801700P	2000-05-26	2000-05-26
PCT/US2001/016566 WO2001092230A1 (en)	2000-05-26	2001-05-22	5-chloro-3-(4-methanesulfonylphenyl)-6'-methyl- [2,3']bipyridinyl in pure crystalline form and process for synthesis

Publications (1)

Publication Number	Publication Date
UA73355C2 true UA73355C2 (en)	2005-07-15

Family

ID=22772880

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20021210537A UA73355C2 (en)	2000-05-26	2001-05-22	5-chlorine-3(4-methanesulfonylphenyl)-6'-methyl-[2,3']pyridinyl in pure crystallyne shape and a method for synthesis

Country Status (49)

Country	Link
EP (1)	EP1296951B1 (es)
JP (2)	JP3665053B2 (es)
KR (1)	KR100757699B1 (es)
CN (1)	CN1227233C (es)
AR (1)	AR028577A1 (es)
AT (1)	ATE483687T1 (es)
AU (2)	AU6480401A (es)
BG (1)	BG65855B1 (es)
BR (1)	BRPI0111140B8 (es)
CA (1)	CA2410234C (es)
CR (1)	CR6606A (es)
CY (1)	CY1111440T1 (es)
CZ (1)	CZ20023888A3 (es)
DE (1)	DE60143197D1 (es)
DK (1)	DK1296951T3 (es)
EA (1)	EA004809B1 (es)
EE (1)	EE05242B1 (es)
EG (1)	EG24189A (es)
ES (1)	ES2351958T3 (es)
GC (1)	GC0000362A (es)
GE (1)	GEP20053492B (es)
GT (1)	GT200100091A (es)
HK (1)	HK1058932A1 (es)
HN (1)	HN2001000110A (es)
HR (1)	HRP20020934B1 (es)
HU (1)	HU228423B1 (es)
IL (1)	IL152582A0 (es)
IN (2)	IN2002CH02089A (es)
IS (1)	IS2806B (es)
JO (1)	JO2216B1 (es)
MA (1)	MA26919A1 (es)
ME (1)	ME00428B (es)
MX (1)	MX230696B (es)
MY (1)	MY123569A (es)
NO (1)	NO324495B1 (es)
NZ (1)	NZ522394A (es)
PA (1)	PA8516901A1 (es)
PE (1)	PE20011324A1 (es)
PH (1)	PH12001001175B1 (es)
PL (1)	PL358153A1 (es)
PT (1)	PT1296951E (es)
RS (1)	RS51541B (es)
SI (1)	SI1296951T1 (es)
SK (1)	SK287174B6 (es)
SV (1)	SV2002000462A (es)
TW (1)	TWI303634B (es)
UA (1)	UA73355C2 (es)
WO (1)	WO2001092230A1 (es)
ZA (1)	ZA200209558B (es)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4425514B2 (ja)	1999-11-29	2010-03-03	メルクフロストカナダリミテツド	５−クロロ−３−（４−メタンスルホニルフェニル）−６′−メチル−［２，３′］ビピリジニルの多形型、非晶質型および水和型
US6858631B1 (en)	1999-11-29	2005-02-22	Merck & Co., Inc.	Polymorphic, amorphous and hydrated forms of 5-chloro-3-(4-methanesulfonylphenyl)-6′-methyl-[2,3′]bipyridinyl
US6521642B2 (en) *	2000-05-26	2003-02-18	Merck & Co., Inc.	5-chloro-3-(4-methanesulfonylphenyl)-6′-methyl-[2,3′]bipyridinyl in pure crystalline form and process for synthesis
HUE028730T2 (en)	2009-02-27	2017-01-30	Cadila Healthcare Ltd	Process for the preparation of etoricoxib
WO2012004677A1 (en)	2010-07-05	2012-01-12	Actavis Group Ptc Ehf	Solid state forms of etoricoxib salts
PL2714676T3 (pl)	2011-05-27	2019-10-31	Farma Grs D O O	Sposób wytwarzania formy polimorficznej I etorykoksybu
EP2773618A1 (en)	2011-11-03	2014-09-10	Cadila Healthcare Limited	An improved process for the preparation of etoricoxib and polymorphs thereof
WO2013075732A1 (en)	2011-11-21	2013-05-30	Synthon Bv	Process for making crystalline form i of etoricoxib
EP2601952A1 (en)	2011-12-07	2013-06-12	Zentiva, k.s.	Novel pharmaceutically acceptable salts and cocrystals of 5-chloro-3-(4-methanesulfonylphenyl)-6'-methyl-[2,3']bipyridinyl and their therapeutic uses
EP2888231B1 (en)	2012-08-27	2019-01-09	Glenmark Pharmaceuticals Limited	Process for preparation of crystalline etoricoxib
EP2887924B1 (en)	2012-08-27	2017-03-29	Cadila Healthcare Limited	Pharmaceutical compositions of etoricoxib
CN104418799A (zh) *	2013-09-03	2015-03-18	天津药物研究院	一种依托考昔的晶型及其制备方法和应用
WO2015036550A1 (en)	2013-09-13	2015-03-19	Synthon B.V.	Process for making etoricoxib
CN106632003B (zh) *	2015-12-31	2019-02-12	上海博志研新药物技术有限公司	一种依托考昔的制备方法
CN108069896B (zh) *	2016-11-11	2022-08-12	昆明积大制药股份有限公司	一种依托考昔晶型的制备方法
CN107056691B (zh) *	2017-06-21	2020-03-10	四川尚锐生物医药有限公司	一种制备依托考昔晶型v的方法
CN107417599B (zh) *	2017-06-21	2020-06-09	四川尚锐生物医药有限公司	一种依托考昔晶型的制备方法
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Publication number	Publication date
JP2004501116A (ja)	2004-01-15
HK1058932A1 (en)	2004-06-11
BRPI0111140B8 (pt)	2021-05-25
NO324495B1 (no)	2007-10-29
ZA200209558B (en)	2003-10-28
EA004809B1 (ru)	2004-08-26
IS2806B (is)	2012-09-15
BG107237A (bg)	2003-05-30
SI1296951T1 (sl)	2011-01-31
AU6480401A (en)	2001-12-11
PE20011324A1 (es)	2002-01-28
EE05242B1 (et)	2009-12-15
KR20030003762A (ko)	2003-01-10
CN1227233C (zh)	2005-11-16
SV2002000462A (es)	2002-03-08
AU2001264804B2 (en)	2006-04-06
SK287174B6 (sk)	2010-02-08
CY1111440T1 (el)	2015-08-05
PL358153A1 (en)	2004-08-09
CA2410234C (en)	2008-05-13
PT1296951E (pt)	2010-12-07
JP3665053B2 (ja)	2005-06-29
EP1296951B1 (en)	2010-10-06
SK16702002A3 (sk)	2003-05-02
MX230696B (es)	2005-09-19
CA2410234A1 (en)	2001-12-06
IL152582A0 (en)	2003-05-29
DE60143197D1 (de)	2010-11-18
JO2216B1 (en)	2004-10-07
CN1443168A (zh)	2003-09-17
CR6606A (es)	2006-02-06
JP4142621B2 (ja)	2008-09-03
EP1296951A1 (en)	2003-04-02
HUP0302336A2 (hu)	2003-11-28
MY123569A (en)	2006-05-31
PH12001001175B1 (en)	2006-08-10
DK1296951T3 (da)	2011-01-24
NZ522394A (en)	2004-05-28
EG24189A (en)	2008-10-08
ES2351958T3 (es)	2011-02-14
GC0000362A (en)	2007-03-31
IN2002CH02089A (es)	2005-02-25
IS6630A (is)	2002-11-20
HRP20020934B1 (en)	2012-01-31
PA8516901A1 (es)	2002-04-25
ATE483687T1 (de)	2010-10-15
MA26919A1 (fr)	2004-12-20
AR028577A1 (es)	2003-05-14
BRPI0111140B1 (pt)	2018-03-13
TWI303634B (en)	2008-12-01
HN2001000110A (es)	2002-03-06
KR100757699B1 (ko)	2007-09-13
NO20025674L (no)	2002-11-26
NO20025674D0 (no)	2002-11-26
RS51541B (sr)	2011-06-30
EA200201264A1 (ru)	2003-04-24
ME00428B (me)	2011-10-10
EE200200655A (et)	2004-08-16
IN2007CH05103A (es)	2008-08-27
HRP20020934A2 (en)	2005-02-28
MXPA02011619A (es)	2003-03-27
BR0111140A (pt)	2005-01-11
WO2001092230A1 (en)	2001-12-06
JP2005047927A (ja)	2005-02-24
BG65855B1 (bg)	2010-03-31
GEP20053492B (en)	2005-04-25
CZ20023888A3 (cs)	2003-02-12
HU228423B1 (en)	2013-03-28
GT200100091A (es)	2001-12-28
YU89402A (sh)	2005-11-28

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