BG107813A - Ефективен метод за получаване на фактор xа инхибитор - Google Patents

Ефективен метод за получаване на фактор xа инхибитор Download PDF

Info

Publication number: BG107813A
Authority: BG; Bulgaria
Prior art keywords: compound; formula; solvent; reacting; water
Prior art date: 2000-09-22

Application number

BG107813A

Other languages

Bulgarian (bg)

English (en)

Inventor

Luigi Anzalone

Fuqiang Jin

David J. Meloni

Jung-Hui Sun

Christopher A. Teleha

Jiacheng Zhou

Thomas E. Smyser

Hui-Yin Li

Original Assignee

Bristol-Myers Squibb Pharma Company

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.)

2000-09-22

Filing date

2003-05-13

Publication date

2004-01-30

2003-05-13 Application filed by Bristol-Myers Squibb Pharma Company filed Critical Bristol-Myers Squibb Pharma Company

2004-01-30 Publication of BG107813A publication Critical patent/BG107813A/bg

Links

238000000034 method Methods 0.000 title claims abstract description 50
238000002360 preparation method Methods 0.000 title claims abstract description 24
230000008569 process Effects 0.000 title claims abstract description 14
229940123583 Factor Xa inhibitor Drugs 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 172
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 43
239000002904 solvent Substances 0.000 claims description 43
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 41
238000006243 chemical reaction Methods 0.000 claims description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 20
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 12
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 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 10
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 8
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
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UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 7
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 7
239000012190 activator Substances 0.000 claims description 7
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239000012453 solvate Substances 0.000 claims description 6
PDBXHPORMXSXKO-UHFFFAOYSA-N 8-benzyl-7-[2-[ethyl(2-hydroxyethyl)amino]ethyl]-1,3-dimethylpurine-2,6-dione;hydron;chloride Chemical compound Cl.N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CCN(CCO)CC)C=1CC1=CC=CC=C1 PDBXHPORMXSXKO-UHFFFAOYSA-N 0.000 claims description 5
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239000000543 intermediate Substances 0.000 abstract description 4
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NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 6
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MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
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DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
229910021515 thallium hydroxide Inorganic materials 0.000 description 1
DASUJKKKKGHFBF-UHFFFAOYSA-L thallium(i) carbonate Chemical compound [Tl+].[Tl+].[O-]C([O-])=O DASUJKKKKGHFBF-UHFFFAOYSA-L 0.000 description 1
QGYXCSSUHCHXHB-UHFFFAOYSA-M thallium(i) hydroxide Chemical compound [OH-].[Tl+] QGYXCSSUHCHXHB-UHFFFAOYSA-M 0.000 description 1
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125000003396 thiol group Chemical group [H]S* 0.000 description 1
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YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
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235000012141 vanillin Nutrition 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
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BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
229960001600 xylazine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

BG107813A 2000-09-22 2003-05-13 Ефективен метод за получаване на фактор xа инхибитор BG107813A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US23462200P	2000-09-22	2000-09-22
PCT/US2001/028406 WO2002024690A2 (en)	2000-09-22	2001-09-12	Efficient process for the preparation of a factor xa inhibitor

Publications (1)

Publication Number	Publication Date
BG107813A true BG107813A (bg)	2004-01-30

Family

ID=22882119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG107813A BG107813A (bg)	2000-09-22	2003-05-13	Ефективен метод за получаване на фактор xа инхибитор

Country Status (23)

Country	Link
US (3)	US6667332B2 (et)
EP (1)	EP1366045A2 (et)
JP (1)	JP2004529853A (et)
KR (1)	KR20040043089A (et)
CN (1)	CN1610679A (et)
AU (1)	AU2001292612A1 (et)
BG (1)	BG107813A (et)
BR (1)	BR0114102A (et)
CA (1)	CA2424576A1 (et)
CZ (1)	CZ2003835A3 (et)
EE (1)	EE200300116A (et)
HR (1)	HRP20030316A2 (et)
HU (1)	HUP0500133A2 (et)
IL (1)	IL155043A0 (et)
IS (1)	IS6754A (et)
MX (1)	MXPA03002493A (et)
NO (1)	NO20031308L (et)
PL (1)	PL366027A1 (et)
RU (1)	RU2003111464A (et)
SK (1)	SK4892003A3 (et)
TW (1)	TW593314B (et)
WO (1)	WO2002024690A2 (et)
ZA (1)	ZA200302971B (et)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6339099B1 (en) *	1997-06-20	2002-01-15	Dupont Pharmaceuticals Company	Guanidine mimics as factor Xa inhibitors
WO2002006218A2 (en) *	2000-07-18	2002-01-24	Bone Care International, Inc.	STABILIZED 1α-HYDROXY VITAMIN D
TW200302225A (en) *	2001-12-04	2003-08-01	Bristol Myers Squibb Co	Substituted amino methyl factor Xa inhibitors
US20040067995A1 (en) *	2002-10-02	2004-04-08	Wong Pancras C.	Novel combination of a factor Xa inhibitor and clopidogrel
JP4435691B2 (ja) *	2002-11-06	2010-03-24	パナソニック株式会社	変位検出機能を備えたマイクロアクチュエータ、および当該マイクロアクチュエータを備えた可変形ミラー
US7429581B2 (en) *	2002-12-23	2008-09-30	Sanofi-Aventis Deutschland Gmbh	Pyrazole-derivatives as factor Xa inhibitors
US20050059719A1 (en) *	2003-09-16	2005-03-17	Badawy Sherif Ibrahim Farag	Solid dosage formulation containing a Factor Xa inhibitor and method
MY199131A (en)	2014-03-07	2023-10-17	Biocryst Pharm Inc	Human plasma kallikrein inhibitors
CN119626346B (zh) *	2025-02-14	2025-05-06	四川省肿瘤医院	一种医学基因测序数据的模式识别方法及设备

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6020357A (en) *	1996-12-23	2000-02-01	Dupont Pharmaceuticals Company	Nitrogen containing heteroaromatics as factor Xa inhibitors
ZA985247B (en) *	1997-06-19	1999-12-17	Du Pont Merck Pharma	Guanidine mimics as factor Xa inhibitors.
US6339099B1 (en) *	1997-06-20	2002-01-15	Dupont Pharmaceuticals Company	Guanidine mimics as factor Xa inhibitors

2001
- 2001-09-12 IL IL15504301A patent/IL155043A0/xx unknown
- 2001-09-12 AU AU2001292612A patent/AU2001292612A1/en not_active Abandoned
- 2001-09-12 BR BR0114102-3A patent/BR0114102A/pt not_active IP Right Cessation
- 2001-09-12 EE EEP200300116A patent/EE200300116A/et unknown
- 2001-09-12 CA CA002424576A patent/CA2424576A1/en not_active Abandoned
- 2001-09-12 HU HU0500133A patent/HUP0500133A2/hu unknown
- 2001-09-12 RU RU2003111464/04A patent/RU2003111464A/ru not_active Application Discontinuation
- 2001-09-12 HR HR20030316A patent/HRP20030316A2/hr not_active Application Discontinuation
- 2001-09-12 EP EP01972987A patent/EP1366045A2/en not_active Withdrawn
- 2001-09-12 CZ CZ2003835A patent/CZ2003835A3/cs unknown
- 2001-09-12 JP JP2002529100A patent/JP2004529853A/ja active Pending
- 2001-09-12 PL PL01366027A patent/PL366027A1/xx not_active Application Discontinuation
- 2001-09-12 KR KR10-2003-7004196A patent/KR20040043089A/ko not_active Withdrawn
- 2001-09-12 WO PCT/US2001/028406 patent/WO2002024690A2/en not_active Ceased
- 2001-09-12 MX MXPA03002493A patent/MXPA03002493A/es unknown
- 2001-09-12 CN CNA018193064A patent/CN1610679A/zh active Pending
- 2001-09-12 SK SK489-2003A patent/SK4892003A3/sk not_active Application Discontinuation
- 2001-09-21 US US09/960,040 patent/US6667332B2/en not_active Expired - Fee Related
- 2001-09-21 TW TW090123363A patent/TW593314B/zh not_active IP Right Cessation
2003
- 2003-03-21 NO NO20031308A patent/NO20031308L/no not_active Application Discontinuation
- 2003-03-21 IS IS6754A patent/IS6754A/is unknown
- 2003-04-15 ZA ZA200302971A patent/ZA200302971B/en unknown
- 2003-05-07 US US10/431,265 patent/US6747158B2/en not_active Expired - Fee Related
- 2003-05-13 BG BG107813A patent/BG107813A/bg unknown
2004
- 2004-04-15 US US10/826,099 patent/US20040198787A1/en not_active Abandoned

Also Published As

Publication number	Publication date
RU2003111464A (ru)	2004-10-27
IL155043A0 (en)	2003-10-31
NO20031308D0 (no)	2003-03-21
US6667332B2 (en)	2003-12-23
CA2424576A1 (en)	2002-03-28
US20020061917A1 (en)	2002-05-23
EE200300116A (et)	2005-04-15
WO2002024690A8 (en)	2002-08-08
IS6754A (is)	2003-03-21
ZA200302971B (en)	2005-05-09
HUP0500133A2 (hu)	2005-04-28
SK4892003A3 (en)	2004-04-06
TW593314B (en)	2004-06-21
HRP20030316A2 (en)	2005-02-28
WO2002024690A3 (en)	2003-09-25
EP1366045A2 (en)	2003-12-03
CN1610679A (zh)	2005-04-27
PL366027A1 (en)	2005-01-24
NO20031308L (no)	2003-05-07
KR20040043089A (ko)	2004-05-22
JP2004529853A (ja)	2004-09-30
AU2001292612A1 (en)	2002-04-02
US6747158B2 (en)	2004-06-08
US20030212117A1 (en)	2003-11-13
MXPA03002493A (es)	2004-09-10
WO2002024690A2 (en)	2002-03-28
CZ2003835A3 (cs)	2003-12-17
BR0114102A (pt)	2005-04-19
US20040198787A1 (en)	2004-10-07

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