ZA200103206B - Novel N-(iminomethyl)amine derivatives, their preparations, their use as medicines and compositions containing them. - Google Patents

Novel N-(iminomethyl)amine derivatives, their preparations, their use as medicines and compositions containing them. Download PDF

Info

Publication number: ZA200103206B
Authority: ZA; South Africa
Prior art keywords: radical; amino; phenyl; carbon atoms; linear
Prior art date: 1998-09-23

Application number

ZA200103206A

Other languages

English (en)

Inventor

Dennis Bigg

Serge Auvin

Jeremiah Harnett

Pierre-Etienne Cha Lassauniere

Gerard Ulibarri

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.)

1998-09-23

Filing date

2001-04-19

Publication date

2002-07-19

2001-04-19 Application filed by Sod Conseils Rech Applic filed Critical Sod Conseils Rech Applic

2002-07-19 Publication of ZA200103206B publication Critical patent/ZA200103206B/en

Links

239000000203 mixture Substances 0.000 title claims description 29
239000003814 drug Substances 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title description 21
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229940079593 drug Drugs 0.000 title 1
-1 phenylene radical Chemical class 0.000 claims description 157
125000004432 carbon atom Chemical group C* 0.000 claims description 103
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 101
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
125000000217 alkyl group Chemical group 0.000 claims description 60
150000003254 radicals Chemical class 0.000 claims description 56
150000001875 compounds Chemical class 0.000 claims description 48
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
229930192474 thiophene Natural products 0.000 claims description 23
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 11
108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 11
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 9
NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 claims description 9
JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
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229910052739 hydrogen Inorganic materials 0.000 claims description 7
BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
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230000000694 effects Effects 0.000 claims description 5
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150000005840 aryl radicals Chemical class 0.000 claims description 4
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125000005842 heteroatom Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
238000010586 diagram Methods 0.000 description 68
239000000543 intermediate Substances 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
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238000003786 synthesis reaction Methods 0.000 description 40
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230000015572 biosynthetic process Effects 0.000 description 30
150000001412 amines Chemical class 0.000 description 28
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 17
230000008018 melting Effects 0.000 description 16
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000000843 powder Substances 0.000 description 12
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000009467 reduction Effects 0.000 description 9
150000007513 acids Chemical class 0.000 description 7
150000003857 carboxamides Chemical class 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000003642 reactive oxygen metabolite Substances 0.000 description 7
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
238000010511 deprotection reaction Methods 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000003480 eluent Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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238000013019 agitation Methods 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
125000004659 aryl alkyl thio group Chemical group 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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150000004820 halides Chemical class 0.000 description 4
238000010647 peptide synthesis reaction Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
VYOKOQDVBBWPKO-UHFFFAOYSA-N 1-nitro-9h-carbazole Chemical class N1C2=CC=CC=C2C2=C1C([N+](=O)[O-])=CC=C2 VYOKOQDVBBWPKO-UHFFFAOYSA-N 0.000 description 3
BXIQHVVAHDCWFM-UHFFFAOYSA-N 2-(4-aminophenyl)-n-(4-anilinophenyl)acetamide Chemical compound C1=CC(N)=CC=C1CC(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 BXIQHVVAHDCWFM-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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125000003277 amino group Chemical group 0.000 description 3
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
238000001035 drying Methods 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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239000002243 precursor Substances 0.000 description 3
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230000008569 process Effects 0.000 description 3
YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 2
FSDLLJPIBXWYSL-UHFFFAOYSA-N 1-[2-[4-[[amino(thiophen-2-yl)methylidene]amino]phenyl]ethyl]-3-(4-anilinophenyl)urea;hydrochloride Chemical compound Cl.C=1C=CSC=1C(=N)NC(C=C1)=CC=C1CCNC(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 FSDLLJPIBXWYSL-UHFFFAOYSA-N 0.000 description 2
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AVDLFIONKHGQAP-UHFFFAOYSA-N 4-nitrophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1 AVDLFIONKHGQAP-UHFFFAOYSA-N 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
208000014644 Brain disease Diseases 0.000 description 2
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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QVCHUOXTWNURMO-UHFFFAOYSA-N n-(4-anilinophenyl)-2-(4-nitrophenyl)acetamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 QVCHUOXTWNURMO-UHFFFAOYSA-N 0.000 description 2
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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150000003672 ureas Chemical class 0.000 description 2
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OEPZMGBENPIQEP-UHFFFAOYSA-N (4-anilinophenyl)carbamic acid;hydrochloride Chemical compound Cl.C1=CC(NC(=O)O)=CC=C1NC1=CC=CC=C1 OEPZMGBENPIQEP-UHFFFAOYSA-N 0.000 description 1
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XHLXYKAMKREIJK-UHFFFAOYSA-N 1-(4-anilinophenyl)-3-[2-(4-nitrophenyl)ethyl]urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1CCNC(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 XHLXYKAMKREIJK-UHFFFAOYSA-N 0.000 description 1
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VWOJSRICSKDKAW-UHFFFAOYSA-N 1-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 VWOJSRICSKDKAW-UHFFFAOYSA-N 0.000 description 1
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230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
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
230000009385 viral infection Effects 0.000 description 1

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ZA200103206A 1998-09-23 2001-04-19 Novel N-(iminomethyl)amine derivatives, their preparations, their use as medicines and compositions containing them. ZA200103206B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9811867A FR2784678B1 (fr)	1998-09-23	1998-09-23	Nouveaux derives de n-(iminomethyl)amines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant

Publications (1)

Publication Number	Publication Date
ZA200103206B true ZA200103206B (en)	2002-07-19

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ZA200103206A ZA200103206B (en)	1998-09-23	2001-04-19	Novel N-(iminomethyl)amine derivatives, their preparations, their use as medicines and compositions containing them.

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US (5)	US6482822B1 (de)
EP (1)	EP1115720B1 (de)
JP (1)	JP2003517444A (de)
KR (1)	KR100655340B1 (de)
CN (1)	CN1144799C (de)
AR (1)	AR024837A1 (de)
AT (1)	ATE399774T1 (de)
AU (1)	AU759958B2 (de)
BR (1)	BR9913899A (de)
CA (1)	CA2344223A1 (de)
CZ (1)	CZ299664B6 (de)
DE (1)	DE69939021D1 (de)
DK (1)	DK1115720T3 (de)
ES (1)	ES2310045T3 (de)
FR (1)	FR2784678B1 (de)
HK (1)	HK1043365B (de)
HU (1)	HUP0104013A3 (de)
IL (2)	IL141997A0 (de)
MY (1)	MY123219A (de)
NO (1)	NO328466B1 (de)
NZ (1)	NZ511188A (de)
PL (1)	PL347471A1 (de)
PT (1)	PT1115720E (de)
RU (1)	RU2230742C2 (de)
WO (1)	WO2000017191A2 (de)
ZA (1)	ZA200103206B (de)

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JPH08504798A (ja) *	1992-12-18	1996-05-21	ザウエルカムファウンデーションリミテッド	酵素阻害薬としての，ピリミジン，ピリジン，プテリジノンおよびインダゾール誘導体
DK0690851T3 (da) *	1993-03-23	1999-11-08	Astra Ab	Guanidin-derivater, som er anvendelige til behandling
GB9312761D0 (en) *	1993-06-21	1993-08-04	Wellcome Found	Amino acid derivatives
US5807885A (en) *	1993-08-12	1998-09-15	Astra Aktiebolag	Amidine derivatives with nitric oxide synthetase activities
WO1996001817A1 (en) *	1994-05-07	1996-01-25	Astra Aktiebolag	Bicyclic amidine derivatives as inhibitors of nitric oxide synthetase
AU2629795A (en) *	1994-12-12	1996-07-03	Chugai Seiyaku Kabushiki Kaisha	Aniline derivative having the effect of inhibiting nitrogen monoxide synthase
FR2761066B1 (fr) *	1997-03-24	2000-11-24	Sod Conseils Rech Applic	Nouveaux derives du 2-(iminomethyl)amino-phenyle, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant
CA2340912C (en) *	1998-08-20	2008-11-18	University Of North Carolina At Chapel Hill	Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof

1998
- 1998-09-23 FR FR9811867A patent/FR2784678B1/fr not_active Expired - Fee Related
1999
- 1999-09-21 AR ARP990104748A patent/AR024837A1/es active IP Right Grant
- 1999-09-22 HU HU0104013A patent/HUP0104013A3/hu unknown
- 1999-09-22 ES ES99943025T patent/ES2310045T3/es not_active Expired - Lifetime
- 1999-09-22 PL PL99347471A patent/PL347471A1/xx unknown
- 1999-09-22 DE DE69939021T patent/DE69939021D1/de not_active Expired - Lifetime
- 1999-09-22 US US09/787,466 patent/US6482822B1/en not_active Expired - Fee Related
- 1999-09-22 PT PT99943025T patent/PT1115720E/pt unknown
- 1999-09-22 JP JP2000574100A patent/JP2003517444A/ja active Pending
- 1999-09-22 AU AU56315/99A patent/AU759958B2/en not_active Ceased
- 1999-09-22 RU RU2001111023/04A patent/RU2230742C2/ru not_active IP Right Cessation
- 1999-09-22 MY MYPI99004105A patent/MY123219A/en unknown
- 1999-09-22 BR BR9913899-9A patent/BR9913899A/pt not_active Application Discontinuation
- 1999-09-22 IL IL14199799A patent/IL141997A0/xx unknown
- 1999-09-22 CN CNB998127523A patent/CN1144799C/zh not_active Expired - Fee Related
- 1999-09-22 EP EP99943025A patent/EP1115720B1/de not_active Expired - Lifetime
- 1999-09-22 NZ NZ511188A patent/NZ511188A/en not_active IP Right Cessation
- 1999-09-22 CZ CZ20011056A patent/CZ299664B6/cs not_active IP Right Cessation
- 1999-09-22 WO PCT/FR1999/002251 patent/WO2000017191A2/fr not_active Ceased
- 1999-09-22 KR KR1020017003670A patent/KR100655340B1/ko not_active Expired - Fee Related
- 1999-09-22 DK DK99943025T patent/DK1115720T3/da active
- 1999-09-22 AT AT99943025T patent/ATE399774T1/de not_active IP Right Cessation
- 1999-09-22 CA CA002344223A patent/CA2344223A1/fr not_active Abandoned
- 1999-09-22 HK HK02105058.6A patent/HK1043365B/zh not_active IP Right Cessation
2001
- 2001-03-13 IL IL141997A patent/IL141997A/en not_active IP Right Cessation
- 2001-03-22 NO NO20011478A patent/NO328466B1/no not_active IP Right Cessation
- 2001-04-19 ZA ZA200103206A patent/ZA200103206B/en unknown
2002
- 2002-09-26 US US10/255,849 patent/US6620840B1/en not_active Expired - Fee Related
2003
- 2003-07-01 US US10/612,646 patent/US6809090B2/en not_active Expired - Fee Related
2004
- 2004-07-21 US US10/895,578 patent/US20050027009A1/en not_active Abandoned
2005
- 2005-04-26 US US11/114,803 patent/US7186752B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO20011478L (no)	2001-03-22
MY123219A (en)	2006-05-31
NO328466B1 (no)	2010-02-22
KR100655340B1 (ko)	2006-12-08
PL347471A1 (en)	2002-04-08
WO2000017191A2 (fr)	2000-03-30
HUP0104013A2 (hu)	2002-04-29
BR9913899A (pt)	2001-07-03
FR2784678A1 (fr)	2000-04-21
EP1115720B1 (de)	2008-07-02
AR024837A1 (es)	2002-10-30
WO2000017191A3 (fr)	2000-10-26
US6482822B1 (en)	2002-11-19
CN1144799C (zh)	2004-04-07
ES2310045T3 (es)	2008-12-16
US7186752B2 (en)	2007-03-06
IL141997A (en)	2008-07-08
HK1043365B (zh)	2005-01-07
FR2784678B1 (fr)	2002-11-29
IL141997A0 (en)	2002-03-10
CZ20011056A3 (cs)	2002-01-16
US20050027009A1 (en)	2005-02-03
US20050197329A1 (en)	2005-09-08
NZ511188A (en)	2003-08-29
US20040097494A1 (en)	2004-05-20
ATE399774T1 (de)	2008-07-15
NO20011478D0 (no)	2001-03-22
EP1115720A2 (de)	2001-07-18
CA2344223A1 (fr)	2000-03-30
RU2230742C2 (ru)	2004-06-20
AU5631599A (en)	2000-04-10
PT1115720E (pt)	2008-10-08
KR20010085832A (ko)	2001-09-07
US6809090B2 (en)	2004-10-26
HK1043365A1 (en)	2002-09-13
DK1115720T3 (da)	2008-11-03
HUP0104013A3 (en)	2003-01-28
DE69939021D1 (de)	2008-08-14
CZ299664B6 (cs)	2008-10-08
US6620840B1 (en)	2003-09-16
AU759958B2 (en)	2003-05-01
JP2003517444A (ja)	2003-05-27
CN1335841A (zh)	2002-02-13

Publication	Publication Date	Title
US7186752B2 (en)	2007-03-06	Derivatives of N-(iminomethyl)amines, their preparation, their use as medicaments and the pharmaceutical compositions containing them
KR100758763B1 (ko)	2007-09-14	신규한 리포산 유도체, 이들의 제조 방법 및 이들을함유하는 제약 조성물
RU2238939C2 (ru)	2004-10-27	Производные амидинов, соединения, фармацевтическая композиция
US5872115A (en)	1999-02-16	2-ureido-benzamide derivatives
IL131915A (en)	2004-06-01	History of 2-Aminomethyl-Amino-Phenyl, their preparation and use as medicines and pharmaceuticals containing them
US7285664B2 (en)	2007-10-23	Heterocyclic or benzenic derivatives of lipoic acid, their preparation and their use as medicaments
JP2003532703A (ja)	2003-11-05	新規アミノ酸誘導体及びその医薬としての使用
RU2233840C2 (ru)	2004-08-10	Новые производные липоевой кислоты, способ их получения (варианты), фармацевтическая композиция
MXPA01003006A (en)	2001-12-13	Novel n-(iminomethyl)amine derivatives, their preparation, their use as medicines and compositions containing them