NO327786B1 - Krystallinske 1-metylkarbapenemforbindelser - Google Patents

Krystallinske 1-metylkarbapenemforbindelser Download PDF

Info

Publication number: NO327786B1
Authority: NO; Norway
Prior art keywords: compound; crystalline form; crystalline; methylcarbapenem derivative; formula
Prior art date: 1999-07-06

Application number

NO20020030A

Other languages

English (en)

Norwegian (no)

Other versions

NO20020030D0 (no

NO20020030L (no

Inventor

Isao Kawamoto

Yasuo Shimoji

Hiroshi Fukuhara

Original Assignee

Sankyo Co

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.)

1999-07-06

Filing date

2002-01-04

Publication date

2009-09-21

2002-01-04 Application filed by Sankyo Co filed Critical Sankyo Co

2002-01-04 Publication of NO20020030D0 publication Critical patent/NO20020030D0/no

2002-03-05 Publication of NO20020030L publication Critical patent/NO20020030L/no

2009-09-21 Publication of NO327786B1 publication Critical patent/NO327786B1/no

Links

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OIIWPAYIXDCDNL-UHFFFAOYSA-M sodium 3-(trimethylsilyl)propionate Chemical compound [Na+].C[Si](C)(C)CCC([O-])=O OIIWPAYIXDCDNL-UHFFFAOYSA-M 0.000 description 1
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239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
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239000003765 sweetening agent Substances 0.000 description 1
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125000001302 tertiary amino group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO20020030A 1999-07-06 2002-01-04 Krystallinske 1-metylkarbapenemforbindelser NO327786B1 (no)

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Application Number	Priority Date	Filing Date	Title
JP19136899		1999-07-06
PCT/JP2000/004496 WO2001002401A1 (fr)	1999-07-06	2000-07-06	Composes de 1-methylcarbapenem cristallin

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NO20020030D0 NO20020030D0 (no)	2002-01-04
NO20020030L NO20020030L (no)	2002-03-05
NO327786B1 true NO327786B1 (no)	2009-09-21

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EP (1)	EP1193269A4 (xx)
JP (1)	JP3476420B2 (xx)
KR (1)	KR100750552B1 (xx)
CN (2)	CN101077869A (xx)
AU (1)	AU758190B2 (xx)
BR (1)	BR0012253A (xx)
CA (1)	CA2378483C (xx)
CZ (1)	CZ20014731A3 (xx)
HK (1)	HK1044768A1 (xx)
HU (1)	HUP0202255A3 (xx)
IL (2)	IL147214A0 (xx)
MX (1)	MXPA02000061A (xx)
NO (1)	NO327786B1 (xx)
NZ (1)	NZ516310A (xx)
PL (1)	PL352296A1 (xx)
RU (2)	RU2214411C2 (xx)
TR (2)	TR200403436T2 (xx)
TW (1)	TWI250160B (xx)
WO (1)	WO2001002401A1 (xx)
ZA (1)	ZA200110413B (xx)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1208323C (zh) *	1999-04-06	2005-06-29	三共株式会社	α－取代羧酸衍生物
US7041660B2 (en) *	1999-07-06	2006-05-09	Sankyo Company, Limited	Crystalline 1-methylcarbapenem derivatives
EP1227100B1 (en) *	1999-09-30	2004-05-26	Otsuka Kagaku Kabushiki Kaisha	3-cephem derivative crystal and method for preparing the same
UA82824C2 (uk)	2000-06-21	2008-05-26	К'Юбіст Фармасьютікалз, Інк.	Композиція і спосіб поліпшення перорального всмоктування протимікробних засобів
KR100451672B1 (ko) *	2001-06-05	2004-10-08	한미약품 주식회사	결정성 세프디니르 산부가염, 이의 제조방법 및 이를이용한 세프디니르의 제조방법
US20040198973A1 (en) *	2001-08-13	2004-10-07	Tsujii Masahiko	Process for preparation of carbapenem antibiotics
WO2003027067A2 (en) *	2001-09-26	2003-04-03	Merck & Co., Inc.	Process for making carbapenem compounds
HRP20040264B1 (en) *	2001-09-26	2012-07-31	Merck@Sharp@@@Dohme@Corp	Process for making carbapenem compounds
ITMI20012364A1 (it) *	2001-11-09	2003-05-09	Antibioticos Spa	Processo di sintesi della cefixima via alchil-o arilsolfonati
JP2005097278A (ja) *	2003-08-25	2005-04-14	Sankyo Co Ltd	１−メチルカルバペネム化合物の結晶
CN101284831A (zh)	2003-08-25	2008-10-15	三共株式会社	1-甲基碳青霉烯化合物的结晶
US20070249827A1 (en) *	2004-06-02	2007-10-25	Sandoz Ag	Meropenem Intermediatein in Crystalling Form
KR20070112464A (ko) *	2005-03-22	2007-11-26	다이이찌 산쿄 가부시키가이샤	1-알킬피롤리딘 구조를 갖는 카르바페넴 유도체의 제조방법
US8968781B2 (en)	2005-04-29	2015-03-03	Cubist Pharmaceuticals, Inc.	Therapeutic compositions
EP1880997A4 (en) *	2005-05-13	2009-03-11	Daiichi Sankyo Co Ltd	1-METHYLCARBAPENEM COMPOUND CRYSTAL
CN101328179B (zh) *	2007-06-15	2011-01-12	山东轩竹医药科技有限公司	含有氧代氮杂环的巯基吡咯烷培南衍生物
CN101412717B (zh) *	2007-10-19	2011-01-12	山东轩竹医药科技有限公司	含有胍基烷酰胺基杂环的碳青霉烯衍生物
US20110054168A1 (en) *	2008-01-17	2011-03-03	Ayumu Kurimoto	Method for preparing adenine compound
CN102918041A (zh) *	2010-05-21	2013-02-06	山东轩竹医药科技有限公司	碳青霉烯衍生物或其水合物的晶型及其制备方法与用途
US8822445B2 (en) *	2010-06-03	2014-09-02	Xuanzhu Pharma Co., Ltd.	Crystalline form of carbapenem derivative or its hydrates and preparation methods and uses thereof
EP2945929B1 (de) *	2013-01-15	2020-01-22	Merck Patent GmbH	Acylguanidine zur behandlung von arthrose

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4260543A (en)	1978-07-03	1981-04-07	Merck & Co., Inc.	Crystalline N-formimidoyl thienamycin
US4748238A (en)	1984-03-14	1988-05-31	Merck & Co., Inc.	Crystalline 1R,5S,6S,8R-1-methyl-2-(N,N-dimethylcarbamimidoylmethylthio)-6-(1-hydroxyethyl)-1-carbapen-2-em-3-carboxylic acid
US4713451A (en)	1984-04-09	1987-12-15	Merck & Co., Inc.	Crystalline dimethyliminothienamycin
IE60588B1 (en) *	1986-07-30	1994-07-27	Sumitomo Pharma	Carbapenem compound in crystalline form, and its production and use
US4866171A (en)	1987-04-11	1989-09-12	Lederle (Japan), Ltd.	(1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)]thio-6-[R-1-hydroxyethyl]-1-methyl-carbapenum-3-carboxylate
TW209220B (xx) *	1991-11-27	1993-07-11	Manyu Seiyaku Kk
ES2131560T3 (es)	1992-11-17	1999-08-01	Sankyo Co	Derivado de carbapenem cristalino.
JPH06336483A (ja) *	1993-05-26	1994-12-06	Banyu Pharmaceut Co Ltd	アミノアルキルピロリジニルチオカルバペネム誘導体
JPH07291973A (ja) *	1994-04-27	1995-11-07	Banyu Pharmaceut Co Ltd	新規な２−ピロリジニルチオカルバペネム誘導体
JPH09110869A (ja) *	1995-10-23	1997-04-28	Lederle Japan Ltd	カルバペネム化合物
EP0882728B1 (en) *	1995-12-21	2002-09-04	Sankyo Company Limited	1-methylcarbapenem derivatives
JP2955276B2 (ja) *	1997-06-19	1999-10-04	三共株式会社	１−メチルカルバペネム誘導体を含有する抗菌剤

2000
- 2000-07-05 TW TW089113337A patent/TWI250160B/zh not_active IP Right Cessation
- 2000-07-06 JP JP2000204430A patent/JP3476420B2/ja not_active Expired - Fee Related
- 2000-07-06 AU AU58487/00A patent/AU758190B2/en not_active Ceased
- 2000-07-06 EP EP00944289A patent/EP1193269A4/en not_active Withdrawn
- 2000-07-06 RU RU2002100058/04A patent/RU2214411C2/ru not_active IP Right Cessation
- 2000-07-06 NZ NZ516310A patent/NZ516310A/en not_active IP Right Cessation
- 2000-07-06 MX MXPA02000061A patent/MXPA02000061A/es active IP Right Grant
- 2000-07-06 CA CA002378483A patent/CA2378483C/en not_active Expired - Fee Related
- 2000-07-06 WO PCT/JP2000/004496 patent/WO2001002401A1/ja active Application Filing
- 2000-07-06 CZ CZ20014731A patent/CZ20014731A3/cs unknown
- 2000-07-06 KR KR1020027000117A patent/KR100750552B1/ko not_active IP Right Cessation
- 2000-07-06 TR TR2004/03436T patent/TR200403436T2/xx unknown
- 2000-07-06 CN CNA2007101096355A patent/CN101077869A/zh active Pending
- 2000-07-06 PL PL00352296A patent/PL352296A1/xx not_active Application Discontinuation
- 2000-07-06 IL IL14721400A patent/IL147214A0/xx unknown
- 2000-07-06 HU HU0202255A patent/HUP0202255A3/hu unknown
- 2000-07-06 CN CNB008124558A patent/CN100360530C/zh not_active Expired - Fee Related
- 2000-07-06 BR BR0012253-0A patent/BR0012253A/pt not_active Application Discontinuation
- 2000-07-06 TR TR2002/00100T patent/TR200200100T2/xx unknown
2001
- 2001-12-19 ZA ZA200110413A patent/ZA200110413B/xx unknown
- 2001-12-20 IL IL147214A patent/IL147214A/en not_active IP Right Cessation
- 2001-12-28 US US10/034,548 patent/US20020128254A1/en not_active Abandoned
2002
- 2002-01-04 NO NO20020030A patent/NO327786B1/no not_active IP Right Cessation
- 2002-08-26 HK HK02106273.3A patent/HK1044768A1/zh unknown
2003
- 2003-01-27 US US10/351,944 patent/US6924279B2/en not_active Expired - Fee Related
- 2003-04-03 US US10/407,546 patent/US20030232803A1/en not_active Abandoned
- 2003-06-18 RU RU2003118411/04A patent/RU2003118411A/ru not_active Application Discontinuation

Also Published As

Publication number	Publication date
RU2003118411A (ru)	2004-12-20
US20020128254A1 (en)	2002-09-12
BR0012253A (pt)	2002-03-26
ZA200110413B (en)	2003-03-19
NO20020030D0 (no)	2002-01-04
KR100750552B1 (ko)	2007-08-20
CN1372560A (zh)	2002-10-02
NO20020030L (no)	2002-03-05
HUP0202255A3 (en)	2003-10-28
AU758190B2 (en)	2003-03-20
TR200403436T2 (tr)	2005-03-21
NZ516310A (en)	2004-05-28
RU2214411C2 (ru)	2003-10-20
AU5848700A (en)	2001-01-22
US20030232803A1 (en)	2003-12-18
US6924279B2 (en)	2005-08-02
WO2001002401A1 (fr)	2001-01-11
IL147214A0 (en)	2002-08-14
CZ20014731A3 (cs)	2002-04-17
HK1044768A1 (zh)	2002-11-01
PL352296A1 (en)	2003-08-11
TR200200100T2 (tr)	2002-05-21
IL147214A (en)	2009-12-24
US20030158174A1 (en)	2003-08-21
CN100360530C (zh)	2008-01-09
HUP0202255A2 (en)	2002-10-28
CA2378483C (en)	2008-09-16
TWI250160B (en)	2006-03-01
EP1193269A4 (en)	2003-05-28
KR20020022761A (ko)	2002-03-27
JP2001072681A (ja)	2001-03-21
JP3476420B2 (ja)	2003-12-10
CA2378483A1 (en)	2001-01-11
CN101077869A (zh)	2007-11-28
EP1193269A1 (en)	2002-04-03
MXPA02000061A (es)	2002-07-02

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JPWO2009075323A1 (ja)	2011-04-28	β−ラクタム化合物の安定形結晶
JP2002029972A (ja)	2002-01-29	カルバペネムエステル化合物を含有する抗菌剤

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