NO326981B1 - Sukkersubstituerte 2-azetidinoner anvendelige som hypokolesterolemiske midler, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament - Google Patents

Sukkersubstituerte 2-azetidinoner anvendelige som hypokolesterolemiske midler, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament Download PDF

Info

Publication number: NO326981B1
Authority: NO; Norway
Prior art keywords: alkyl; group; substituted; independently selected; halogen
Prior art date: 2000-12-20

Application number

NO20032806A

Other languages

English (en)

Norwegian (no)

Other versions

NO20032806L (no

NO20032806D0 (no

Inventor

Harry R Davis

James E Patrick

Anima Ghosal

Shmuel Zbaida

Swapan K Chowdhury

Robert M Iannucci

Wenqing Feng

Kevin B Alton

Original Assignee

Schering Corp

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.)

2000-12-20

Filing date

2003-06-19

Publication date

2009-03-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22973953&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO326981(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2003-06-19 Application filed by Schering Corp filed Critical Schering Corp

2003-06-19 Publication of NO20032806D0 publication Critical patent/NO20032806D0/no

2003-08-19 Publication of NO20032806L publication Critical patent/NO20032806L/no

2009-03-30 Publication of NO326981B1 publication Critical patent/NO326981B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 60
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title claims description 27
239000000825 pharmaceutical preparation Substances 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title claims description 9
239000003814 drug Substances 0.000 title claims description 8
229940079593 drug Drugs 0.000 title claims description 5
239000003529 anticholesteremic agent Substances 0.000 title description 5
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 claims description 118
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 69
235000012000 cholesterol Nutrition 0.000 claims description 42
230000015572 biosynthetic process Effects 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000003112 inhibitor Substances 0.000 claims description 31
-1 -OH Inorganic materials 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 29
150000002367 halogens Chemical class 0.000 claims description 29
125000003118 aryl group Chemical group 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 17
201000001320 Atherosclerosis Diseases 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
239000003937 drug carrier Substances 0.000 claims description 14
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
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 claims description 11
229960002855 simvastatin Drugs 0.000 claims description 11
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 claims description 11
241000124008 Mammalia Species 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 6
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 6
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 6
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 6
229960005370 atorvastatin Drugs 0.000 claims description 6
229960003765 fluvastatin Drugs 0.000 claims description 6
229960004844 lovastatin Drugs 0.000 claims description 6
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical group C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 6
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 6
229960002965 pravastatin Drugs 0.000 claims description 6
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
KIRGLCXNEVICOG-SOFGYWHQSA-N (e)-n-ethyl-6,6-dimethyl-n-[[3-[(4-thiophen-3-ylthiophen-2-yl)methoxy]phenyl]methyl]hept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(CC)CC1=CC=CC(OCC=2SC=C(C=2)C2=CSC=C2)=C1 KIRGLCXNEVICOG-SOFGYWHQSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229960002797 pitavastatin Drugs 0.000 claims description 5
VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims description 5
RHGYHLPFVJEAOC-FFNUKLMVSA-L pitavastatin calcium Chemical compound [Ca+2].[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1.[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 RHGYHLPFVJEAOC-FFNUKLMVSA-L 0.000 claims description 5
229960000672 rosuvastatin Drugs 0.000 claims description 5
DFKDOZMCHOGOBR-NCSQYGPNSA-N zaragozic acid A Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CC[C@]12[C@H](O)[C@H]([C@](O2)(C(O)=O)[C@@](O)([C@H](O1)C(O)=O)C(O)=O)OC(=O)/C=C/[C@@H](C)C[C@@H](C)CC)C1=CC=CC=C1 DFKDOZMCHOGOBR-NCSQYGPNSA-N 0.000 claims description 5
DFKDOZMCHOGOBR-UHFFFAOYSA-N zaragozic acid A Natural products O1C(C(O)(C(O2)C(O)=O)C(O)=O)(C(O)=O)C(OC(=O)C=CC(C)CC(C)CC)C(O)C21CCC(=C)C(OC(C)=O)C(C)CC1=CC=CC=C1 DFKDOZMCHOGOBR-UHFFFAOYSA-N 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000003003 spiro group Chemical group 0.000 claims description 2
125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
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ODCZJZWSXPVLAW-KXCGKLMDSA-N Hymeglusin Chemical compound OC(=O)/C=C(\C)/C=C(C)/C[C@H](C)CCCC[C@H]1OC(=O)[C@@H]1CO ODCZJZWSXPVLAW-KXCGKLMDSA-N 0.000 claims 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 16
238000000034 method Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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NO20032806A 2000-12-20 2003-06-19 Sukkersubstituerte 2-azetidinoner anvendelige som hypokolesterolemiske midler, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament NO326981B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US25687500P	2000-12-20	2000-12-20
PCT/US2001/049127 WO2002050090A1 (en)	2000-12-20	2001-12-17	Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents

Publications (3)

Publication Number	Publication Date
NO20032806D0 NO20032806D0 (no)	2003-06-19
NO20032806L NO20032806L (no)	2003-08-19
NO326981B1 true NO326981B1 (no)	2009-03-30

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Application Number	Title	Priority Date	Filing Date
NO20032806A NO326981B1 (no)	2000-12-20	2003-06-19	Sukkersubstituerte 2-azetidinoner anvendelige som hypokolesterolemiske midler, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament
NO20083737A NO20083737L (no)	2000-12-20	2008-08-29	Hydroksysubstituerte 2-azetidinoner som er anvendbare som hypokolesterolemiske midler

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NO20083737A NO20083737L (no)	2000-12-20	2008-08-29	Hydroksysubstituerte 2-azetidinoner som er anvendbare som hypokolesterolemiske midler

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US (1)	US20020137690A1 (ru)
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DE (2)	DE60129863T2 (ru)
DK (2)	DK1347987T3 (ru)
EC (1)	ECSP034659A (ru)
ES (2)	ES2230385T3 (ru)
GE (1)	GEP20053548B (ru)
HU (1)	HUP0302269A3 (ru)
IL (1)	IL155771A0 (ru)
MA (1)	MA26975A1 (ru)
MX (1)	MXPA03005671A (ru)
MY (1)	MY129148A (ru)
NO (2)	NO326981B1 (ru)
NZ (1)	NZ525722A (ru)
PE (1)	PE20020718A1 (ru)
PL (1)	PL208242B1 (ru)
PT (2)	PT1347987E (ru)
RU (1)	RU2297422C2 (ru)
SI (2)	SI1593670T1 (ru)
SK (1)	SK286703B6 (ru)
TR (1)	TR200402758T4 (ru)
TW (1)	TWI316942B (ru)
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AU2002231049B2 (en)	2006-07-20
RU2003122520A (ru)	2005-02-27
PL208242B1 (pl)	2011-04-29
SK286703B6 (sk)	2009-03-05
GEP20053548B (en)	2005-06-27
CY1106912T1 (el)	2012-09-26
DE60129863T2 (de)	2008-04-30
NO20083737L (no)	2003-08-19
MA26975A1 (fr)	2004-12-20
US20020137690A1 (en)	2002-09-26
RU2297422C2 (ru)	2007-04-20
WO2002050090A1 (en)	2002-06-27
WO2002050090A8 (en)	2004-04-15
CZ302193B6 (cs)	2010-12-08
CN100475829C (zh)	2009-04-08
ZA200303694B (en)	2004-08-13
CN1483039A (zh)	2004-03-17
SI1347987T1 (en)	2005-02-28
DE60106489D1 (de)	2004-11-18
TR200402758T4 (tr)	2004-11-22
MXPA03005671A (es)	2003-10-06
KR20030063414A (ko)	2003-07-28
DK1593670T3 (da)	2007-11-05
TWI316942B (en)	2009-11-11
HUP0302269A3 (en)	2009-08-28
CZ20031674A3 (cs)	2003-10-15
BR0116212A (pt)	2003-12-30
ES2230385T3 (es)	2005-05-01
ATE279425T1 (de)	2004-10-15
ES2287826T3 (es)	2007-12-16
EP1347987A1 (en)	2003-10-01
HK1056735A1 (en)	2004-02-27
EP1347987B1 (en)	2004-10-13
JP2009132745A (ja)	2009-06-18
NZ525722A (en)	2004-11-26
AU3104902A (en)	2002-07-01
MY129148A (en)	2007-03-30
AR035611A1 (es)	2004-06-16
DE60106489T2 (de)	2005-10-13
CA2432798A1 (en)	2002-06-27
PE20020718A1 (es)	2002-08-09
JP2004516299A (ja)	2004-06-03
DE60129863D1 (de)	2007-09-20
NO20032806L (no)	2003-08-19
DK1347987T3 (da)	2005-01-31
PL363237A1 (en)	2004-11-15
PT1347987E (pt)	2005-01-31
SI1593670T1 (sl)	2007-12-31
JP4351842B2 (ja)	2009-10-28
NO20032806D0 (no)	2003-06-19
IL155771A0 (en)	2003-12-23
KR100883461B1 (ko)	2009-02-16
CA2432798C (en)	2007-02-27
ATE369334T1 (de)	2007-08-15
HUP0302269A2 (hu)	2003-10-28
HK1084945A1 (en)	2006-08-11
PT1593670E (pt)	2007-11-08
ECSP034659A (es)	2003-07-25
SK7702003A3 (en)	2003-10-07

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Owner name: MERCK SHARP AND DOHME CORP

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Publication	Publication Date	Title
NO326981B1 (no)	2009-03-30	Sukkersubstituerte 2-azetidinoner anvendelige som hypokolesterolemiske midler, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament
CA2235943C (en)	2002-10-01	Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents
US6982251B2 (en)	2006-01-03	Substituted 2-azetidinones useful as hypocholesterolemic agents
EP1593670B1 (en)	2007-08-08	Hydroxy-substituted 2-azetidinones useful as hypocholesterolemic agents
EP1510521A1 (en)	2005-03-02	Sugar-substituted 2-Azetidinones useful as hypocholesterolemic agents
HK1084945B (en)	2008-01-04	Hydroxy-substituted 2-azetidinones useful as hypocholesterolemic agents
HK1073315A (en)	2005-09-30	Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents
HK1056735B (en)	2005-05-06	Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents