TW577885B - Imidazolyl derivatives, pharmaceutical composition comprising the same and process for synthesizing thereof - Google Patents

Imidazolyl derivatives, pharmaceutical composition comprising the same and process for synthesizing thereof Download PDF

Info

Publication number: TW577885B
Authority: TW; Taiwan
Prior art keywords: group; compound; synthesizing; alkyl; same
Prior art date: 1998-06-16

Application number

TW088110018A

Other languages

English (en)

Inventor

Zheng-Xin Dong

Yeelana Shen

Original Assignee

Sod Conseils Rech Applic

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.)

1998-06-16

Filing date

1999-08-19

Publication date

2004-03-01

1999-08-19 Application filed by Sod Conseils Rech Applic filed Critical Sod Conseils Rech Applic

2004-03-01 Application granted granted Critical

2004-03-01 Publication of TW577885B publication Critical patent/TW577885B/zh

Links

125000002883 imidazolyl group Chemical group 0.000 title abstract 2
238000000034 method Methods 0.000 title description 4
230000002194 synthesizing effect Effects 0.000 title description 4
239000008194 pharmaceutical composition Substances 0.000 title 1
102000005454 Dimethylallyltranstransferase Human genes 0.000 abstract 1
108010006731 Dimethylallyltranstransferase Proteins 0.000 abstract 1
239000003558 transferase inhibitor Substances 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 11
239000000126 substance Substances 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 8
238000010586 diagram Methods 0.000 description 7
230000002079 cooperative effect Effects 0.000 description 5
150000001412 amines Chemical group 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
-1 stilbyl Chemical group 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000000719 pyrrolidinyl group Chemical group 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1

Classifications

- 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
- C07D401/14—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 three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- A61P31/10—Antimycotics
- 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
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- C07D403/14—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 three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Oncology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Communicable Diseases (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Virology (AREA)
Vascular Medicine (AREA)
Ophthalmology & Optometry (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

Description

577885 A8 BS C8 D8 申請奉利範圍 ' R7、R8及R9每一者係個別選自H&C1-C4烷基所組成之群組 * 9 R10係選自胺基及羥基所構成之群組； R18為C1-C4烷基； R19係個別選自Η、Κ4烷基、咄嗅基、嗎啉基及吼咯啶基所構成之群組； R20及 R21 — 起形成二價基-(CH2)r-NR37-(CH2)s-，其中 r及s 係每一者個別為1至3 ; 以及R37為Η或是當其與鄰近的氮原子一同形成 ----------, — ΙΊ-裝—— (請先閱讀背面之注意事寫本頁) 經濟部智慧財產局員工消費合作社印製 2. 如申請專利範圍第1項之化合物，其中R1、R2、R3、R· \ R12及R13每一者係氯基或氫。 3. 如申請專利範圍第2項之化合物，其中R7、R8及每一者係C 1 - C 4烧基或氮。 4·如申請專利範圍第3項之化合物，其中R7、R8及R9每一者係甲基或氫。 5.如申請專利範圍第4項之化合物 6·如申請專利範圍第5項之化合物 7.如申請專利範圍第6項之化合物，其中γ係η、曱基、 s(〇)2r18 或 c(〇)nr20r21。 8·如申請專利範圍第7項之化合物，其中該化合物為如下化學式者：其中R1Q係〇H或胺基其中Z係氫。訂· _線. 577885 A8 B8 C8 D8 、申請專利範圍經濟部智慧財產局員工消費合作社印製

其中R1Q係〇H且丫係Η ; R10係 ΝΗ2且 Υ係-S(〇)2-CH3 ; R10係〇H且丫係-S(〇)2-CH3 ; R10係〇H且丫係-0(0)^(0^)2 ; R10係 NH2且丫係-C(〇)-N(CH3)2 ; R10係NH2且丫係H ; R1Q係〇H且丫係 -C(0)-N、 -C(〇)-N、 R1Q係NH2且丫係 R10係〇H且丫係-C(〇）-N(CH2CH3)2 ; R10係 NH2且 Y係-(：(〇)-Ν(〇Η2〇Η3)2 ; R10係〇H且丫係-CH3 ;或 R10係 NH2且丫係-CH3。 9.如申請專利範圍第8項之化合物，其中該化合物係如下之化學式：本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐）

(請先閱讀背面之注意事X —裝--- I填寫本頁) 訂·- --線· 577885 A8 B8 C8 D8 申請奉利範圍

Cl

Cl R10係〇H且丫係Η ;R10係 1^2且丫係-S(〇)2-CH3 ;R10係〇H且 Y係-S(0)2-CH3 ;或 R10係 OH且 Y係 _C(〇)-N(CH3)2。 10·如申請專利範圍第9項之化合物，其中該化合物係如下之化學式：、 (請先閱讀背面之注意事寫本頁) 裝訂·

GI 線· 經濟部智慧財產局員工消費合作社印製 R1Q係〇Η且丫係Η ;或 R10 係0Η 且丫係-S(〇)2_CH3者。 11 · 一種合成化學式3之化合物之方法，其係依據下述示意圖，其包含使依據下述示意圖之化學式1之化合物與依楗下述示意圖之化學式2之^'烧基錤氯化物反應，其中X3係c卜Mg 且p = 1-2，或與化學式2之芳基鋰反應，其間X3係Li且P==0 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 577885 Α8 Β8 C8 D8 、申請奉利範圍 ' ，其係於惰性有機溶劑中為之，至反應實質完成為止，

(請先閱讀背面之注意事寫本頁) 裝訂- 其中p係保護基； m、η、p及 q為〇 ; 丁被省略； X 係 N-Y，其中 Y係選自 Η、CH3、S(〇)2R18、C(〇)R19及C(〇)NR20R21 所構成之群組； Z係選自Η及i基所構成之群組； R1、R2、R3、R11、R12及R13之每一者係個別選自Η及鹵基所構成之群組； R4、R5及R6係各自選自Η; R7、R8及R9每一者係個別選自Η或匕-匕烷基；本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐〉 -線· 經濟部智慧財產局員工消費合作社印製 5 577885 A8 B8 C8 D8 、申請奉利範圍 ' R1C)係選自胺基與羥基所構成的群組； R18係CrQ烷基； R19係個別選自Η、CrC4烷基、咄啶基、嗎啉基及吡咯啶基所構成之群組； R20及R21 —起形成二價基-(CH2)rNR37T(CH2)s-，其中r及s每一者係個別為1至3;以及 / \ 37 N 〇 / R37係1-1或與鄰接的1\|原子形成\~丨。 12. —種依據下述示意圖合成化學式2之化合物之方法，其包含使依據下示示意圖之化學式1之化合物與氯化劑反應至反應實質被完成為之， (請先閱讀背面之注意事寫本頁) 裝訂經濟部智慧財產局員工消費合作社印製

R4 •線· 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 577885 A8

BS C8 D8 申請奉利範圍其中m、η、p及q為〇 ; Τ被省略； X 係 Ν-Υ，其中 Υ係選自 Η、CH3、S(〇)2R18、C(〇)R19及C(0)NR20R21 所構成之群組； z係選自Η及齒基所構成之群組； R、R、R、R、R12及R13之每—者係個別選自基所構成之群組； R4、R5及R6係各自選自H; R7、R8及R9每一者係個別選自H或…心烷基； R1Q係選自胺基及羥基所構成之群組； R18係Κ4烧基； R係個別選自Η、CrC4烷基、吡啶基、嗎啉基及咄咯啶基所構成之群組； R20及R21 —起形成二價基_(CH2)rNR37-(CH2V，其中「及3每—者係個別為1至3 ;以及 R係η或與鄰接的N原子形成。經濟部智慧財產局員工消費合作社印製 13· 一種依據下述示意圖合成化學式3之化合物之方法，其使依據下示示意圖之化學式2之化合物與無水之液態以無水氨飽和之惰性有機溶劑反應，其中n，卩及^之每係0，或與氫氧化銨反應（當n，p，q之每一者係不至反應實質被完成為之，本紙張尺度適用中家標準（CNS)A4規格（21Q χ 297公[ 577885 Α8 Β8 C8 D8 六、申請辜利範圍

----------‘丨·!裝--- (請先閲讀背面之注意事寫本頁) 訂· 經濟部智慧財產局員工消費合作社印製其中m、η、p及q為〇 ; T被省略； X 係 N-Y，其中 Y係選自 Η、CH3、S(〇)2R18、C(〇)R19或C(〇)NR20R21 所組成之群組； Z係選自Η及鹵基所組成之群組； R1、R2、R3、R11、R12及R13之每一者係個別選自Η或鹵基所組成之群組； R4、R5及R6係各自選自Η; R7、R8及R9每一者係個別選自Η或GrC4烧基； R1Q係選自Η或胺基所組成之群組； _i紙張尺度適用中關家標準（CNS)A4規格⑽> 577885 Α8 Β8 C8 D8 、申請奉利範圍 R18係CrC4烷基； R 9係個別選自Η、Ci -C4烧基、吼σ定基、嗎琳基及吼哈。定基所構成之群組； R20及R21 —起形成二價基-(CH2)r-NR37-(CH2)s-，其中r及s每一者係個別為1至3 ;以及 / \ q7 N 〇 R37係Η或與鄰接的N原子形成\~。 (請先閱讀背面之注意事寫本頁) 裝訂- 線· 經濟部智慧財產局員工消費合作社印製本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐）

TW088110018A 1998-06-16 1999-08-19 Imidazolyl derivatives, pharmaceutical composition comprising the same and process for synthesizing thereof TW577885B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US9814198A	1998-06-16	1998-06-16
US8948398P	1998-06-16	1998-06-16

Publications (1)

Publication Number	Publication Date
TW577885B true TW577885B (en)	2004-03-01

Family

ID=26780620

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW088110018A TW577885B (en)	1998-06-16	1999-08-19	Imidazolyl derivatives, pharmaceutical composition comprising the same and process for synthesizing thereof

Country Status (12)

Country	Link
EP (1)	EP1097150B1 (zh)
JP (1)	JP2002518387A (zh)
AR (1)	AR019866A1 (zh)
AT (1)	ATE262520T1 (zh)
AU (1)	AU4822299A (zh)
CA (1)	CA2335435A1 (zh)
DE (1)	DE69915835T2 (zh)
DK (1)	DK1097150T3 (zh)
ES (1)	ES2216535T3 (zh)
NO (1)	NO320835B1 (zh)
TW (1)	TW577885B (zh)
WO (1)	WO1999065898A1 (zh)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2825706B1 (fr) *	2001-06-06	2003-12-12	Pf Medicament	Nouveaux derives de benzothienyle ou d'indole, leur preparation et leur utilisation comme inhibiteurs de proteines prenyl transferase

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2002859C (en) *	1988-11-29	1998-12-29	Jean P. F. Van Wauwe	Method of treating epithelial disorders
GB9212833D0 (en) *	1992-06-17	1992-07-29	Glaxo Group Ltd	Chemical compounds
TW316902B (zh) *	1994-12-28	1997-10-01	Janssen Pharmaceutica Nv
US5756528A (en) *	1995-06-06	1998-05-26	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
TW349948B (en) *	1995-10-31	1999-01-11	Janssen Pharmaceutica Nv	Farnesyl transferase inhibiting 2-quinolone derivatives
DE69620445T2 (de) *	1995-12-08	2002-12-12	Janssen Pharmaceutica N.V., Beerse	(imidazol-5-yl)methyl-2-chinolinoderivate als farnesyl protein transferase inhibitoren
AU706150B2 (en) *	1996-04-03	1999-06-10	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
TW591030B (en) *	1997-03-10	2004-06-11	Janssen Pharmaceutica Nv	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with N- or C-linked imidazoles

1999
- 1999-06-11 CA CA002335435A patent/CA2335435A1/en not_active Abandoned
- 1999-06-11 WO PCT/US1999/013303 patent/WO1999065898A1/en not_active Ceased
- 1999-06-11 ES ES99931792T patent/ES2216535T3/es not_active Expired - Lifetime
- 1999-06-11 DK DK99931792T patent/DK1097150T3/da active
- 1999-06-11 AT AT99931792T patent/ATE262520T1/de not_active IP Right Cessation
- 1999-06-11 DE DE69915835T patent/DE69915835T2/de not_active Expired - Fee Related
- 1999-06-11 JP JP2000554723A patent/JP2002518387A/ja active Pending
- 1999-06-11 AU AU48222/99A patent/AU4822299A/en not_active Abandoned
- 1999-06-11 EP EP99931792A patent/EP1097150B1/en not_active Expired - Lifetime
- 1999-06-15 AR ARP990102856A patent/AR019866A1/es unknown
- 1999-08-19 TW TW088110018A patent/TW577885B/zh not_active IP Right Cessation
2000
- 2000-12-15 NO NO20006401A patent/NO320835B1/no unknown

Also Published As

Publication number	Publication date
EP1097150A1 (en)	2001-05-09
ATE262520T1 (de)	2004-04-15
ES2216535T3 (es)	2004-10-16
EP1097150B1 (en)	2004-03-24
DE69915835T2 (de)	2005-03-24
WO1999065898A1 (en)	1999-12-23
AR019866A1 (es)	2002-03-20
NO20006401L (no)	2000-12-15
NO20006401D0 (no)	2000-12-15
JP2002518387A (ja)	2002-06-25
AU4822299A (en)	2000-01-05
DE69915835D1 (de)	2004-04-29
CA2335435A1 (en)	1999-12-23
DK1097150T3 (da)	2004-07-26
NO320835B1 (no)	2006-01-30

Legal Events

Date	Code	Title	Description
2008-02-11	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
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NO20080157L (no)	2008-01-09	Fremgangsmate for syntese av organiske forbindelser
NO20055226L (no)	2005-11-07	Fremgangsmate for fremstilling av N-substituerte 2-cyanopyrrolidoner
KR830007638A (ko)	1983-11-04	2-구아니디노-4-헤테로아릴티아졸의 제조방법
TW577885B (en)	2004-03-01	Imidazolyl derivatives, pharmaceutical composition comprising the same and process for synthesizing thereof
SE7704783L (sv)	1978-10-27	Medel for separationsendamal och forfarande for dess framstellning
KR910016695A (ko)	1991-11-05	4-(아미노메틸) 피페리딘 유도체, 그의 제조방법 및 치료에의 이용
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