SK242004A3 - Methyl analogs of simvastatin as novel HMG-CoA reductase inhibitors - Google Patents

Methyl analogs of simvastatin as novel HMG-CoA reductase inhibitors Download PDF

Info

Publication number: SK242004A3
Authority: SK; Slovakia
Prior art keywords: solvent; organic solvent; methyl; simvastatin; vii
Prior art date: 2001-06-13

Application number

SK24-2004A

Other languages

English (en)

Slovak (sk)

Inventor

Rajesh Kumar Thaper

Saridi Madhava Dileep Kumar

Original Assignee

Ranbaxy Lab Ltd

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.)

2001-06-13

Filing date

2002-06-10

Publication date

2004-06-08

2002-06-10 Application filed by Ranbaxy Lab Ltd filed Critical Ranbaxy Lab Ltd

2004-06-08 Publication of SK242004A3 publication Critical patent/SK242004A3/sk

Links

125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 17
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 title claims abstract description 14
229960002855 simvastatin Drugs 0.000 title claims abstract description 14
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 title claims abstract description 13
229940121710 HMGCoA reductase inhibitor Drugs 0.000 title description 3
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 title description 3
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 19
208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 5
238000011282 treatment Methods 0.000 claims abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
239000002798 polar solvent Substances 0.000 claims description 8
239000012296 anti-solvent Substances 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 5
238000000605 extraction Methods 0.000 claims description 5
239000012022 methylating agents‎ Substances 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
FJDQVJUXXNIHNB-UHFFFAOYSA-N lithium;pyrrolidin-1-ide Chemical group [Li+].C1CC[N-]C1 FJDQVJUXXNIHNB-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
239000011928 denatured alcohol Substances 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims 1
238000000638 solvent extraction Methods 0.000 claims 1
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 15
235000012000 cholesterol Nutrition 0.000 abstract description 6
230000015572 biosynthetic process Effects 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 3
208000020446 Cardiac disease Diseases 0.000 abstract description 2
208000019622 heart disease Diseases 0.000 abstract description 2
238000011321 prophylaxis Methods 0.000 abstract description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 6
108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000007069 methylation reaction Methods 0.000 description 5
FHSAZOGISLHXPK-SCSAIBSYSA-N (3r)-3-hydroxyoxan-2-one Chemical compound O[C@@H]1CCCOC1=O FHSAZOGISLHXPK-SCSAIBSYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
150000002596 lactones Chemical group 0.000 description 4
239000010410 layer Substances 0.000 description 4
230000011987 methylation Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002585 base Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000011161 development Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000005837 enolization reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
-1 for example: Na Chemical class 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
TZIBIGANXIPLNB-UHFFFAOYSA-N lithium;pyrrolidin-2-one Chemical compound [Li].O=C1CCCN1 TZIBIGANXIPLNB-UHFFFAOYSA-N 0.000 description 2
RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
IKAACYWAXDLDPM-UHFFFAOYSA-N 1,2,3,4,4a,5-hexahydronaphthalene Chemical group C1=CCC2CCCCC2=C1 IKAACYWAXDLDPM-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VGMFHMLQOYWYHN-UHFFFAOYSA-N Compactin Natural products OCC1OC(OC2C(O)C(O)C(CO)OC2Oc3cc(O)c4C(=O)C(=COc4c3)c5ccc(O)c(O)c5)C(O)C(O)C1O VGMFHMLQOYWYHN-UHFFFAOYSA-N 0.000 description 1
206010020961 Hypocholesterolaemia Diseases 0.000 description 1
102000004316 Oxidoreductases Human genes 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-HQMMCQRPSA-N acetic acid Chemical compound C[14C](O)=O QTBSBXVTEAMEQO-HQMMCQRPSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011324 bead Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
150000004074 biphenyls Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000005515 coenzyme Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
150000001261 hydroxy acids Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 1
BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK24-2004A 2001-06-13 2002-06-10 Methyl analogs of simvastatin as novel HMG-CoA reductase inhibitors SK242004A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IN659DE2001		2001-06-13
PCT/IB2002/002112 WO2002100323A2 (en)	2001-06-13	2002-06-10	METHYL ANALOGS OF SIMVASTATIN AS NOVEL HMG-CoA REDUCTASE INHIBITORS

Publications (1)

Publication Number	Publication Date
SK242004A3 true SK242004A3 (en)	2004-06-08

Family

ID=11097071

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK24-2004A SK242004A3 (en)	2001-06-13	2002-06-10	Methyl analogs of simvastatin as novel HMG-CoA reductase inhibitors

Country Status (12)

Country	Link
US (1)	US6541511B1 (cs)
EP (1)	EP1404313A4 (cs)
JP (1)	JP2005500282A (cs)
CN (1)	CN1535145A (cs)
BR (1)	BR0210426A (cs)
CA (1)	CA2450617A1 (cs)
CZ (1)	CZ200450A3 (cs)
EA (1)	EA200400034A1 (cs)
PL (1)	PL367885A1 (cs)
SK (1)	SK242004A3 (cs)
WO (1)	WO2002100323A2 (cs)
ZA (1)	ZA200400017B (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101126084B1 (ko) *	2008-11-04	2012-03-29	한미홀딩스 주식회사	(3ｓ,4ｓ)-4-((ｒ)-2-(벤질옥시)트라이데실)-3-헥실-2-옥세타논의 제조방법 및 이에 사용되는 중간체
CN102086184A (zh) *	2011-03-03	2011-06-08	上海应用技术学院	5位氟取代的4-羟基-3,4,5,6-四氢-2h-吡喃-2-酮类化合物及其制备方法
US9499621B2 (en)	2013-04-08	2016-11-22	Cytodyn, Inc.	Felinized antibodies and methods of treating retroviral infections in felines
ES2524647B1 (es)	2013-06-06	2015-09-15	Neuron Bio, S.A.	Compuestos neuroprotectores, antiinflamatorios y antiepilépticos

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2748825C2 (de)	1976-11-02	1986-11-27	Sankyo Co., Ltd., Tokio/Tokyo	Substituierte 3,5-Dihydroxyheptansäurederivate und diese enthaltende Arzneimittel gegen Hyperlipämie
ES8105781A1 (es)	1979-07-27	1981-06-16	Sankyo Co	Un procedimiento para la preparacion de sales y esteres, de monacolina k utiles como agentes antitlipercolesteremicos.
JPS56142236A (en)	1980-04-08	1981-11-06	Sankyo Co Ltd	Ml-236a and mb-530a derivative
US4343814A (en)	1980-11-17	1982-08-10	Merck & Co., Inc.	Hypocholesterolemic fermentation products
EP0068038B1 (en)	1981-06-29	1985-09-25	Merck & Co. Inc.	(+)-(4r,6s)-(e)-6-(2-(4'-fluoro-3,3',5-trimethyl-(1,1'-biphenyl)-2-yl)ethenyl)-3,4,5,6-tetrahydro-4-hydroxy-2h-pyran-2-one, a process for preparing and a pharmaceutical composition containing the same
US4582915A (en) *	1983-10-11	1986-04-15	Merck & Co., Inc.	Process for C-methylation of 2-methylbutyrates
US6376683B1 (en) *	2001-06-01	2002-04-23	Council Of Scientific & Industrial Research	Process for the preparation of (4R,6S)-4-hydroxy-6-hydroxymethyl-tetrahydropyran-2-one

2002
- 2002-06-10 CA CA002450617A patent/CA2450617A1/en not_active Abandoned
- 2002-06-10 JP JP2003503150A patent/JP2005500282A/ja active Pending
- 2002-06-10 BR BR0210426-1A patent/BR0210426A/pt not_active Application Discontinuation
- 2002-06-10 EA EA200400034A patent/EA200400034A1/ru unknown
- 2002-06-10 WO PCT/IB2002/002112 patent/WO2002100323A2/en not_active Ceased
- 2002-06-10 CZ CZ200450A patent/CZ200450A3/cs unknown
- 2002-06-10 US US10/166,468 patent/US6541511B1/en not_active Expired - Fee Related
- 2002-06-10 PL PL02367885A patent/PL367885A1/xx not_active Application Discontinuation
- 2002-06-10 SK SK24-2004A patent/SK242004A3/sk unknown
- 2002-06-10 EP EP02733152A patent/EP1404313A4/en not_active Withdrawn
- 2002-06-10 CN CNA028144600A patent/CN1535145A/zh active Pending
2004
- 2004-01-05 ZA ZA200400017A patent/ZA200400017B/en unknown

Also Published As

Publication number	Publication date
CA2450617A1 (en)	2002-12-19
BR0210426A (pt)	2004-08-17
US6541511B1 (en)	2003-04-01
JP2005500282A (ja)	2005-01-06
EP1404313A4 (en)	2006-01-18
CN1535145A (zh)	2004-10-06
EP1404313A2 (en)	2004-04-07
ZA200400017B (en)	2004-10-25
CZ200450A3 (cs)	2004-05-12
EA200400034A1 (ru)	2004-06-24
PL367885A1 (en)	2005-03-07
WO2002100323A2 (en)	2002-12-19
WO2002100323A3 (en)	2003-09-18

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