UA75353C2 - N-[2-hydroxy-3-(1-piperidinyl)propoxy]piridine-1-oxide-3-carboxamidine and a method for transformation thereof into pharmaceutically effective compounds - Google Patents

N-[2-hydroxy-3-(1-piperidinyl)propoxy]piridine-1-oxide-3-carboxamidine and a method for transformation thereof into pharmaceutically effective compounds Download PDF

Info

Publication number: UA75353C2
Authority: UA; Ukraine
Prior art keywords: pyridine; oxide; hydroxy; piperidinyl; propoxy
Prior art date: 2000-04-18

Application number

UA2002108255A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Biorex Kutato Fejlesztoe Kft

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.)

2000-04-18

Filing date

2001-04-17

Publication date

2006-04-17

2001-04-17 Application filed by Biorex Kutato Fejlesztoe Kft filed Critical Biorex Kutato Fejlesztoe Kft

2006-04-17 Publication of UA75353C2 publication Critical patent/UA75353C2/uk

Links

238000000034 method Methods 0.000 title claims description 23
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 title abstract description 48
230000009466 transformation Effects 0.000 title description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 44
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 27
239000002585 base Substances 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 15
-1 alkali metal nitrite Chemical class 0.000 claims description 13
238000006193 diazotization reaction Methods 0.000 claims description 13
238000000926 separation method Methods 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
230000003993 interaction Effects 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
239000000654 additive Substances 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
230000001131 transforming effect Effects 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 26
239000004480 active ingredient Substances 0.000 abstract description 4
239000000126 substance Substances 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 20
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000000047 product Substances 0.000 description 12
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 8
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
230000003287 optical effect Effects 0.000 description 7
WOOVSQCALYYUDO-UHFFFAOYSA-N 1-oxidopyridin-1-ium-3-carbonitrile Chemical compound [O-][N+]1=CC=CC(C#N)=C1 WOOVSQCALYYUDO-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
150000007522 mineralic acids Chemical class 0.000 description 5
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
239000000155 melt Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
150000002688 maleic acid derivatives Chemical class 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000004965 peroxy acids Chemical class 0.000 description 3
230000010287 polarization Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
QRGUYOXSVWPAGG-UHFFFAOYSA-N n'-hydroxy-1-oxidopyridin-1-ium-3-carboximidamide Chemical compound ON=C(N)C1=CC=C[N+]([O-])=C1 QRGUYOXSVWPAGG-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical class C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 description 1
KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000002249 Diabetes Complications Diseases 0.000 description 1
206010012655 Diabetic complications Diseases 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
206010022489 Insulin Resistance Diseases 0.000 description 1
102000005431 Molecular Chaperones Human genes 0.000 description 1
108010006519 Molecular Chaperones Proteins 0.000 description 1
ZTRUGGRWJFSFFF-UHFFFAOYSA-N N'-hydroxy-1-oxidopyridin-1-ium-2-carboximidamide Chemical compound ON=C(N)C1=CC=CC=[N+]1[O-] ZTRUGGRWJFSFFF-UHFFFAOYSA-N 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000011978 dissolution method Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
BSPDRIFPGZTCND-UHFFFAOYSA-N pyridine-3-carboximidoyl chloride Chemical compound ClC(=N)C1=CC=CN=C1 BSPDRIFPGZTCND-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UA2002108255A 2000-04-18 2001-04-17 N-[2-hydroxy-3-(1-piperidinyl)propoxy]piridine-1-oxide-3-carboxamidine and a method for transformation thereof into pharmaceutically effective compounds UA75353C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU0001583A HUP0001583A2 (hu)	2000-04-18	2000-04-18	Egy piridin-1-oxid-származék és eljárás annak átalakítására gyógyászati hatású vegyületekké
PCT/HU2001/000046 WO2001079174A1 (en)	2000-04-18	2001-04-17	A pyridine-1-oxide derivative, and process for its transformation into pharmaceutically effective compounds

Publications (1)

Publication Number	Publication Date
UA75353C2 true UA75353C2 (en)	2006-04-17

Family

ID=90001563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002108255A UA75353C2 (en)	2000-04-18	2001-04-17	N-[2-hydroxy-3-(1-piperidinyl)propoxy]piridine-1-oxide-3-carboxamidine and a method for transformation thereof into pharmaceutically effective compounds

Country Status (31)

Country	Link
US (1)	US7126002B2 (sr)
EP (1)	EP1274685B1 (sr)
JP (1)	JP5066638B2 (sr)
KR (1)	KR100742482B1 (sr)
CN (1)	CN1216868C (sr)
AT (1)	ATE332894T1 (sr)
AU (2)	AU2001254997B2 (sr)
BG (1)	BG65889B1 (sr)
BR (1)	BRPI0110184B8 (sr)
CA (1)	CA2406266C (sr)
CY (1)	CY1107473T1 (sr)
CZ (1)	CZ301576B6 (sr)
DE (1)	DE60121431T2 (sr)
DK (1)	DK1274685T3 (sr)
EE (1)	EE05085B1 (sr)
ES (1)	ES2267758T3 (sr)
HR (1)	HRP20020825A2 (sr)
HU (1)	HUP0001583A2 (sr)
IL (2)	IL152337A0 (sr)
MX (1)	MXPA02010320A (sr)
NO (1)	NO323535B1 (sr)
NZ (1)	NZ522017A (sr)
PL (1)	PL359826A1 (sr)
PT (1)	PT1274685E (sr)
RS (1)	RS51003B (sr)
RU (1)	RU2281282C2 (sr)
SI (1)	SI1274685T1 (sr)
SK (1)	SK287606B6 (sr)
UA (1)	UA75353C2 (sr)
WO (1)	WO2001079174A1 (sr)
ZA (1)	ZA200208460B (sr)

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HUP9900475D0 (en) *	1999-02-26	1999-04-28	Biorex Kutato Fejlesztoe Kft	O-(3-piperidino-2-hydroxy-1-propyl)-hiyroximic acid-halogenid derivative, it's use for treating insulin resistance, and pharmaceutical compositions containing them as active component
HU0103939D0 (en) *	2001-09-27	2001-11-28	Biorex Kutato Fejlesztoe Kft	Pharmaceutical composition containing methformin and n-[2-hydroxy-3-(1-piperidinyl)-propoxy]-pyridine-1-oxide-3-carboximidoyl chloride
CA2471752A1 (en) *	2002-01-11	2003-07-17	Biorex Kutato Es Fejlesztoe Rt.	Carboxamidine derivatives and their use in the treatment of vascular diseases
HUP0303584A3 (en)	2003-10-30	2009-12-28	Cytrx Corp	Use of a hydroximic acid halide derivative in the treatment of neurodegenerative diseases
TW200831479A (en) *	2006-09-26	2008-08-01	Cytrx Corp	Pharmaceutical compositions and methods for treating diseases
EP2484371B1 (en)	2008-06-26	2014-12-17	Orphazyme APS	Use of Hsp70 as a regulator of enzymatic activity
RU2013125923A (ru)	2010-11-30	2015-01-10	Орфазиме Апс	СПОСОБЫ УВЕЛИЧЕНИЯ ВНУТРИКЛЕТОЧНОЙ АКТИВНОСТИ Hsp70
HUP1100535A2 (en)	2011-09-26	2013-04-29	Bracelia Invest Ltd	Pharmaceutical composition for enhancement of stem cell treatment
HUP1100534A2 (en)	2011-09-26	2013-04-29	Balazs Dr Hazay	Pharmaceutical composition for the treatment of muscle atrophy
US10709700B2 (en)	2014-09-15	2020-07-14	Orphazyme A/S	Arimoclomol formulation
EP3442530A1 (en)	2016-04-13	2019-02-20	Orphazyme A/S	Heat shock proteins and cholesterol homeostasis
SI3448382T1 (sl)	2016-04-29	2021-03-31	Orphazyme A/S, c/o COBIS A/S	Arimoclomol za zdravljenje motenj, povezanih z glukocerebrozidazo
AU2018337761C1 (en)	2017-09-22	2025-01-30	Adelaide university	Methods and products for improving sperm quality
HUP1800298A1 (hu)	2018-08-30	2020-05-28	N Gene Res Laboratories Inc	Gyógyszerkombináció béta-receptor blokkolók hatásának módosítására és a mellékhatások csökkentésére
WO2021260120A1 (en)	2020-06-24	2021-12-30	Orphazyme A/S	Arimoclomol for treating gaucher disease
CN116783164A (zh) *	2020-11-19	2023-09-19	泽维拉丹麦股份有限公司	制备柠檬酸阿瑞洛莫及其中间体的方法
WO2022106614A1 (en)	2020-11-19	2022-05-27	Orphazyme A/S	Processes for preparing arimoclomol citrate and intermediates thereof
JP2024502304A (ja)	2020-12-24	2024-01-18	ゼブラデンマークエー／エス	Ｅｒ型ミスセンス変異を有する患者におけるニーマンピック病ｃ型の治療用アリモクロモル
WO2025014519A1 (en)	2023-07-10	2025-01-16	N-Gene Research Laboratories, Inc.	Increasing telomere length and/or suppressing telomere shortening

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU207988B (en) *	1988-10-20	1993-07-28	Biorex Kutato Fejlesztoe Kft	Process for producing halogenides of o-/3-amino-2-hydroxy-propyl/hydroximic acid and pharmaceutical compositions containing them as active components
HU9502843D0 (en)	1995-09-29	1995-11-28	Livigene Ltd	Pharmaceutical composition
HU222994B1 (hu) *	1995-11-02	2004-01-28	BIOREX Kutató és Fejlesztő Rt.	Hidroxilaminszármazékok és azok alkalmazása sejtek molekuláris chaperon-termelésének fokozására alkalmas gyógyszerkészítmények előállítására
HUP9900475D0 (en) *	1999-02-26	1999-04-28	Biorex Kutato Fejlesztoe Kft	O-(3-piperidino-2-hydroxy-1-propyl)-hiyroximic acid-halogenid derivative, it's use for treating insulin resistance, and pharmaceutical compositions containing them as active component

2000
- 2000-04-18 HU HU0001583A patent/HUP0001583A2/hu unknown
2001
- 2001-04-17 RS YUP-783/02A patent/RS51003B/sr unknown
- 2001-04-17 CA CA2406266A patent/CA2406266C/en not_active Expired - Lifetime
- 2001-04-17 RU RU2002130710/04A patent/RU2281282C2/ru not_active IP Right Cessation
- 2001-04-17 UA UA2002108255A patent/UA75353C2/uk unknown
- 2001-04-17 SI SI200130607T patent/SI1274685T1/sl unknown
- 2001-04-17 DK DK01928133T patent/DK1274685T3/da active
- 2001-04-17 MX MXPA02010320A patent/MXPA02010320A/es active IP Right Grant
- 2001-04-17 AU AU2001254997A patent/AU2001254997B2/en not_active Expired
- 2001-04-17 ES ES01928133T patent/ES2267758T3/es not_active Expired - Lifetime
- 2001-04-17 US US10/257,755 patent/US7126002B2/en not_active Expired - Lifetime
- 2001-04-17 WO PCT/HU2001/000046 patent/WO2001079174A1/en not_active Ceased
- 2001-04-17 JP JP2001576775A patent/JP5066638B2/ja not_active Expired - Lifetime
- 2001-04-17 HR HRP20020825 patent/HRP20020825A2/hr not_active Application Discontinuation
- 2001-04-17 EE EEP200200591A patent/EE05085B1/xx not_active IP Right Cessation
- 2001-04-17 SK SK1508-2002A patent/SK287606B6/sk not_active IP Right Cessation
- 2001-04-17 NZ NZ522017A patent/NZ522017A/en unknown
- 2001-04-17 PL PL35982601A patent/PL359826A1/xx not_active IP Right Cessation
- 2001-04-17 IL IL15233701A patent/IL152337A0/xx active IP Right Grant
- 2001-04-17 PT PT01928133T patent/PT1274685E/pt unknown
- 2001-04-17 AT AT01928133T patent/ATE332894T1/de not_active IP Right Cessation
- 2001-04-17 EP EP01928133A patent/EP1274685B1/en not_active Expired - Lifetime
- 2001-04-17 KR KR1020027014047A patent/KR100742482B1/ko not_active Expired - Fee Related
- 2001-04-17 AU AU5499701A patent/AU5499701A/xx active Pending
- 2001-04-17 CZ CZ20023445A patent/CZ301576B6/cs not_active IP Right Cessation
- 2001-04-17 BR BRPI0110184A patent/BRPI0110184B8/pt not_active IP Right Cessation
- 2001-04-17 DE DE60121431T patent/DE60121431T2/de not_active Expired - Lifetime
- 2001-04-17 CN CN018108318A patent/CN1216868C/zh not_active Expired - Lifetime
2002
- 2002-10-16 BG BG107199A patent/BG65889B1/bg unknown
- 2002-10-17 IL IL152337A patent/IL152337A/en unknown
- 2002-10-18 ZA ZA200208460A patent/ZA200208460B/en unknown
- 2002-10-18 NO NO20025015A patent/NO323535B1/no not_active IP Right Cessation
2006
- 2006-07-21 CY CY20061101020T patent/CY1107473T1/el unknown

Also Published As

Publication number	Publication date
AU5499701A (en)	2001-10-30
KR20030011309A (ko)	2003-02-07
ES2267758T3 (es)	2007-03-16
HUP0001583D0 (en)	2000-06-28
ATE332894T1 (de)	2006-08-15
WO2001079174A8 (en)	2002-12-27
WO2001079174A1 (en)	2001-10-25
RS51003B (sr)	2010-10-31
ZA200208460B (en)	2003-10-20
HK1055741A1 (en)	2004-01-21
US7126002B2 (en)	2006-10-24
CZ20023445A3 (cs)	2003-03-12
PL359826A1 (en)	2004-09-06
BG107199A (bg)	2003-07-31
IL152337A0 (en)	2003-05-29
RU2281282C2 (ru)	2006-08-10
SK15082002A3 (sk)	2003-05-02
NO20025015L (no)	2002-12-16
JP2004501080A (ja)	2004-01-15
RU2002130710A (ru)	2004-03-20
SK287606B6 (sk)	2011-03-04
DK1274685T3 (da)	2006-11-06
BRPI0110184B8 (pt)	2021-05-25
EP1274685B1 (en)	2006-07-12
EE05085B1 (et)	2008-10-15
CZ301576B6 (cs)	2010-04-21
HUP0001583A2 (hu)	2002-11-28
MXPA02010320A (es)	2004-09-06
NZ522017A (en)	2004-06-25
AU2001254997B2 (en)	2006-11-23
CN1434800A (zh)	2003-08-06
PT1274685E (pt)	2006-09-29
DE60121431D1 (de)	2006-08-24
EE200200591A (et)	2004-04-15
CA2406266A1 (en)	2001-10-25
BRPI0110184B1 (pt)	2015-12-29
EP1274685A1 (en)	2003-01-15
BR0110184A (pt)	2003-06-17
US20040006232A1 (en)	2004-01-08
BG65889B1 (bg)	2010-04-30
IL152337A (en)	2007-10-31
JP5066638B2 (ja)	2012-11-07
HRP20020825A2 (en)	2004-12-31
CN1216868C (zh)	2005-08-31
NO323535B1 (no)	2007-06-04
DE60121431T2 (de)	2007-01-18
CA2406266C (en)	2010-07-20
KR100742482B1 (ko)	2007-07-25
NO20025015D0 (no)	2002-10-18
YU78302A (sh)	2005-09-19
SI1274685T1 (sl)	2006-10-31
CY1107473T1 (el)	2012-12-19

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RU2026293C1 (ru)	1995-01-09	Способ получения производного имидазола
JPH0474354B2 (sr)	1992-11-26
LU82115A1 (fr)	1980-04-23	Nouvelles quinazolines anti-hypertensives,leur procede de production et composition pharmaceutique les contenant
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JPH01221381A (ja)	1989-09-04	ピラゾロピリミジン類