WO1998050394A1 - Transporteurs de no a base de complexes polyazamacrocycles - Google Patents
Transporteurs de no a base de complexes polyazamacrocycles Download PDFInfo
- Publication number
- WO1998050394A1 WO1998050394A1 PCT/FR1998/000847 FR9800847W WO9850394A1 WO 1998050394 A1 WO1998050394 A1 WO 1998050394A1 FR 9800847 W FR9800847 W FR 9800847W WO 9850394 A1 WO9850394 A1 WO 9850394A1
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- molecule according
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims abstract description 117
- 239000000969 carrier Substances 0.000 title 1
- 239000003814 drug Substances 0.000 claims abstract description 12
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 11
- 241001465754 Metazoa Species 0.000 claims abstract description 10
- 241000282414 Homo sapiens Species 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 5
- 230000002685 pulmonary effect Effects 0.000 claims abstract description 5
- 238000002405 diagnostic procedure Methods 0.000 claims abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 210000000748 cardiovascular system Anatomy 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 210000000987 immune system Anatomy 0.000 claims description 2
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 2
- 210000005227 renal system Anatomy 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 3
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitrogen oxide(NO) Natural products O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 238000004566 IR spectroscopy Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 241000894007 species Species 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 238000013313 FeNO test Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 238000004611 spectroscopical analysis Methods 0.000 description 6
- 238000004435 EPR spectroscopy Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000005292 diamagnetic effect Effects 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002505 iron Chemical class 0.000 description 3
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
- MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 description 2
- PSWDQTMAUUQILQ-UHFFFAOYSA-N 2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C2=CC(OC)=CC=C2N=C1NC1=NC(=O)C(C)=C(C)N1 PSWDQTMAUUQILQ-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- 229940125796 compound 3d Drugs 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002678 macrocyclic compounds Chemical class 0.000 description 2
- 230000009635 nitrosylation Effects 0.000 description 2
- 230000005298 paramagnetic effect Effects 0.000 description 2
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 2
- 229940083618 sodium nitroprusside Drugs 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 description 1
- VQFZKDXSJZVGDA-UHFFFAOYSA-N 1,5,9-triazacyclododecane Chemical compound C1CNCCCNCCCNC1 VQFZKDXSJZVGDA-UHFFFAOYSA-N 0.000 description 1
- ZMOJWEUSGOWQBM-UHFFFAOYSA-N 1-(pyridin-2-ylmethyl)-1,4,8,11-tetrazacyclotetradecane Chemical compound C=1C=CC=NC=1CN1CCCNCCNCCCNCC1 ZMOJWEUSGOWQBM-UHFFFAOYSA-N 0.000 description 1
- WTLKTXIHIHFSGU-UHFFFAOYSA-N 2-nitrosoguanidine Chemical compound NC(N)=NN=O WTLKTXIHIHFSGU-UHFFFAOYSA-N 0.000 description 1
- ZMTZMXMEGARCOT-UHFFFAOYSA-N 3-(1,4,8,11-tetrazacyclotetradec-1-yl)propanoic acid Chemical compound OC(=O)CCN1CCCNCCNCCCNCC1 ZMTZMXMEGARCOT-UHFFFAOYSA-N 0.000 description 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- HAPVSOMXSKSUFV-UHFFFAOYSA-N N(=O)[Co] Chemical compound N(=O)[Co] HAPVSOMXSKSUFV-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- XOWVFANEOZMPKG-REOHCLBHSA-N S-nitroso-L-cysteine Chemical compound OC(=O)[C@@H](N)CSN=O XOWVFANEOZMPKG-REOHCLBHSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- YEESUBCSWGVPCE-UHFFFAOYSA-N azanylidyneoxidanium iron(2+) pentacyanide Chemical compound [Fe++].[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.N#[O+] YEESUBCSWGVPCE-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229960002460 nitroprusside Drugs 0.000 description 1
- -1 nitrosyl metal complex Chemical class 0.000 description 1
- VZQAQPGIOPQBGU-UHFFFAOYSA-N oxidoiminoiron(1+) Chemical compound [Fe]N=O VZQAQPGIOPQBGU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000008695 pulmonary vasoconstriction Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical compound C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 description 1
- RRBYUSWBLVXTQN-VZCHMASFSA-N tricyclene Natural products C([C@@H]12)C3C[C@H]1C2(C)C3(C)C RRBYUSWBLVXTQN-VZCHMASFSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
Definitions
- the present invention relates to new molecules capable of transporting and releasing nitrogen monoxide (NO) in a biological medium, their use for the implementation of a therapeutic treatment method or a diagnostic method applied to the human body or animal, as well as for the manufacture of medicaments which can be used to treat or prevent disorders of the cardiovascular, nervous, immune, renal or pulmonary system in humans or animals.
- NO nitrogen monoxide
- this document suggests coupling the NO molecule to a transporter molecule, which makes it possible to transport NO to its site of use, then release there.
- NO transporters are in particular S-nitrosocysteine, nitroprusside, nitrosoguanidine or azide.
- NO molecule for therapeutic purposes has been the subject of many other documents, for example: WO-A-93/15779, WO-A-94/22499, WO-A-95 / 26768, WO-A-94/00180, WO-A-95/10315.
- Coupling the NO molecule with such a transporter makes it possible to take full advantage of the beneficial therapeutic effects of said NO molecule, without risking poisoning of the patient with NO having been oxidized to NO 2 .
- NO transporter molecule used as a drug is sodium nitroprusside.
- this compound is of considerable therapeutic interest due to its significant vasodilatory activity, it has a major drawback, namely a potential toxicity resulting from the release of cyanide ions; said release of cyanide ions being due, in vivo, to a reaction of sodium nitroprusside with a reducing agent.
- the aim of the present invention is therefore to overcome the problems and drawbacks of the compounds of the prior art, by proposing new molecules making it possible to transport and release the NO molecule to its site of use in the body, which are pharmaceutically acceptable, which are not toxic or which do not release toxic compounds, which make it possible to avoid the oxidation of NO, which have high stability, which are easy to synthesize, store and handle.
- the invention therefore relates to a molecule intended for transporting and releasing nitrogen monoxide (NO) in a biological medium, characterized in that it corresponds to the following formula (I):
- R2, R3 and R4 are groups chosen from the group formed by: the hydrogen atom, and the alkyl groups comprising from 1 to 4 carbon atoms.
- the divalent cation M 2+ is Fe 2+ or Co 2+ -
- the molecule according to the invention will advantageously be chosen from the group formed by:
- the molecules according to the invention may be used for the implementation of a method of therapeutic treatment of the human or animal body, or for the implementation of a diagnostic method applied to the human or animal body.
- the invention also relates to the use of one of the above molecules for the manufacture of a medicament which can be used for the treatment or prevention of disorders of the cardiovascular system, the central or peripheral nervous system, the immune system, the renal system. , or the pulmonary system.
- the metallation reaction is carried out under an inert atmosphere in order to prevent any oxidation of the metal center (Fe or Co).
- the nitrosylation of the complex thus obtained is then carried out under an atmosphere of NO.
- - 333 denotes a 1,5,9-triazacyclododecane
- - 2222 denotes a 1, 4, 7, 10-tetraazacyclododecane or cyclene;
- (2323) -CH 2 -oPy denotes an N- (2-pyridylmethyl) - 1,4,8,11-tetraazacyclotetradecane.
- nitrosylated complexes obtained are characterized by Electronic Paramagnetic Resonance Spectroscopy (RPE) and by Infrared Spectroscopy (IR).
- RPE Electronic Paramagnetic Resonance Spectroscopy
- IR Infrared Spectroscopy
- IR spectroscopy makes it possible to determine the nitrosylated complexes with a bent structure (formally coordination of NO with an electron) and those with a linear structure (formally coordination of NO with three electrons) corresponding to species: N0 ⁇ or N0 + .
- the characterization of the complex by IR spectroscopy also indicates the disappearance of the nitrosyl group coordinated on the metal center.
- nitrosylated iron complexes The synthesis of nitrosylated iron complexes is carried out as follows. 1.5.10 ⁇ 4 mole of ligand (macrocycle) is subjected to a vacuum-argon cycling, intended to remove any trace of undesirable oxygen, then dissolved in 10 ml of methanol previously distilled under an inert atmosphere (argon). To the solution obtained, 1.5.10 " mole of iron chloride dissolved in 4 ml of methanol (step i) is added. The mixture is then sparged with NO gas for approximately 1 minute (step ii ).
- nitrosylated cobalt complexes The synthesis of nitrosylated cobalt complexes is carried out in a similar manner to that of nitrosylated iron complexes, described in example 1, with the difference that it is a 1.5 ⁇ 10 ⁇ 4 mole solution of cobalt chloride which is used ( step i).
- these various nitrolysed metal complexes are subjected to a study of stability, that is to say of reversibility of the nitrosylation reaction.
- the reversibility of this reaction reflects the strength of the metal-NO bond, that is to say the stability of the nitrosyl metal complex, which is a function of the strength of the ligand field. The higher the electron density at the metal, the stronger the metal-NO bond and therefore the stable complex.
- EPR Electronic Paramagnetic Resonance Spectroscopy
- Compound 3d corresponds to the molecule (X) represented above, where the groups R 1; R, R and R 4 are methyl groups.
- RPE spectroscopy no RPE signal observed.
- RPE spectroscopy no RPE signal observed.
- Compounds 4al and 4a2 reversibly fix NO; dissociation is observed under an inert atmosphere (argon).
- compound 4b does not exhibit any reversibility of binding.
- the compounds of the invention are therefore capable of being used, as therapeutic agents, in order to transport and release in vivo the NO molecule which they reversibly fix.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU75363/98A AU7536398A (en) | 1997-05-07 | 1998-04-28 | Nitric oxide carriers based on polyazamacrocycle complexes |
CA002287981A CA2287981A1 (fr) | 1997-05-07 | 1998-04-28 | Transporteurs de no a base de complexes polyazamacrocycles |
US09/423,363 US6310202B1 (en) | 1997-05-07 | 1998-04-28 | Nitric oxide carriers based on polyazamacrocycle complexes |
JP54776998A JP2001524120A (ja) | 1997-05-07 | 1998-04-28 | ポリアザ大環状錯体に基づくnoキャリヤ |
EP98922881A EP0983283A1 (fr) | 1997-05-07 | 1998-04-28 | Transporteurs de no a base de complexes polyazamacrocycles |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9705674A FR2762992B1 (fr) | 1997-05-07 | 1997-05-07 | Transporteurs de no a base de complexes polyazamacrocycles de fer et de cobalt |
FR97/05674 | 1997-05-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998050394A1 true WO1998050394A1 (fr) | 1998-11-12 |
Family
ID=9506700
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1998/000847 WO1998050394A1 (fr) | 1997-05-07 | 1998-04-28 | Transporteurs de no a base de complexes polyazamacrocycles |
Country Status (7)
Country | Link |
---|---|
US (1) | US6310202B1 (fr) |
EP (1) | EP0983283A1 (fr) |
JP (1) | JP2001524120A (fr) |
AU (1) | AU7536398A (fr) |
CA (1) | CA2287981A1 (fr) |
FR (1) | FR2762992B1 (fr) |
WO (1) | WO1998050394A1 (fr) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10226522A1 (de) * | 2002-06-14 | 2003-12-24 | Degussa | Verwendung von Übergangsmetallkomplexen mit stickstoffhaltigen mehrzähnigen Liganden als Bleichkatalysator und Bleichmittelzusammensetzung |
DE10227775A1 (de) * | 2002-06-21 | 2004-02-19 | Degussa Ag | Verwendung von Übergangsmetallkomplexen mit stickstoffhaltigen mehrzähnigen Liganden als Bleichkatalysator und Bleichmittelzusammensetzungen |
DE10227774A1 (de) * | 2002-06-21 | 2004-01-08 | Degussa Ag | Verwendung von Übergangsmetallkomplexen mit stickstoffhaltigen mehrzähnigen Liganden als Bleichkatalysator und Bleichmittelzusammensetzung |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992010228A1 (fr) * | 1990-12-05 | 1992-06-25 | The General Hospital Corporation | Dispositifs utilises pour traiter la vasoconstriction pulmonaire et l'asthme |
WO1994022499A1 (fr) * | 1993-04-06 | 1994-10-13 | Brigham And Womens Hospital | Effets systemiques de l'inhalation de l'oxyde nitrique |
-
1997
- 1997-05-07 FR FR9705674A patent/FR2762992B1/fr not_active Expired - Fee Related
-
1998
- 1998-04-28 CA CA002287981A patent/CA2287981A1/fr not_active Abandoned
- 1998-04-28 US US09/423,363 patent/US6310202B1/en not_active Expired - Fee Related
- 1998-04-28 WO PCT/FR1998/000847 patent/WO1998050394A1/fr not_active Application Discontinuation
- 1998-04-28 EP EP98922881A patent/EP0983283A1/fr not_active Withdrawn
- 1998-04-28 JP JP54776998A patent/JP2001524120A/ja active Pending
- 1998-04-28 AU AU75363/98A patent/AU7536398A/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992010228A1 (fr) * | 1990-12-05 | 1992-06-25 | The General Hospital Corporation | Dispositifs utilises pour traiter la vasoconstriction pulmonaire et l'asthme |
WO1994022499A1 (fr) * | 1993-04-06 | 1994-10-13 | Brigham And Womens Hospital | Effets systemiques de l'inhalation de l'oxyde nitrique |
Non-Patent Citations (10)
Title |
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BR. J. PHARMACOL. (1993), 108(1), 3-5 CODEN: BJPCBM;ISSN: 0007-1188, 1993 * |
CHEMICAL ABSTRACTS, vol. 118, no. 9, 1 March 1993, Columbus, Ohio, US; abstract no. 77939, RAJANAYAGAM, M. A. S. ET AL: "Differential effects of hydroxocobalamin on nitric oxide-mediated relaxations in rat aorta and anococcygeus muscle" XP002053408 * |
CHEMICAL ABSTRACTS, vol. 122, no. 1, 2 January 1995, Columbus, Ohio, US; abstract no. 4628, ANES, J. M. ET AL: "Nitritocobalamin and nitrosocobalamin may be confused with sulfitocobalamin using cation-exchange chromatography" XP002053407 * |
CHEMICAL ABSTRACTS, vol. 82, no. 12, 24 March 1975, Columbus, Ohio, US; abstract no. 79851, LONG, KENNETH M. ET AL: "Cobalt(III) complexes of the tetradentate macrocycle 2,12-dimethyl-3,7,11,17-tetraazabicyclo(11.3.1)heptadeca-1(17), 2,11,13,15-pentaene" XP002053411 * |
CHEMICAL ABSTRACTS, vol. 92, no. 18, 5 May 1980, Columbus, Ohio, US; abstract no. 156150, COOPER, DAVID J. ET AL: "Nitrosylmanganese(II) and -cobalt(II) complexes of a quinquedentate Schiff's base ligand. Crystal and molecular structure of [2,12-di(pyridyl)-3,7,11-triazatrideca-2,11- diene]nitrosylmanganese(II) diperchlorate" XP002053410 * |
CHEMICAL ABSTRACTS, vol. 93, no. 22, 1 December 1980, Columbus, Ohio, US; abstract no. 214649, KOEHLER, H. ET AL: "Metal pseudohalides. Part XXXI. Diamine complexes of nickel(II), cobalt(II), and copper(II) dicyanamide and nitrosodicyanmethanide" XP002053409 * |
J. CHEM. RES., SYNOP. (1979), (9), 287 CODEN: JRPSDC;ISSN: 0308-2342, 1979 * |
J. CHROMATOGR., B: BIOMED. APPL. (1994), 660(1), 180-5 CODEN: JCBBEP, 1994 * |
J. COORD. CHEM. (1974), 4(2), 113-23 CODEN: JCCMBQ, 1974 * |
Z. ANORG. ALLG. CHEM. (1980), 468, 179-84 CODEN: ZAACAB;ISSN: 0044-2313, 1980 * |
Also Published As
Publication number | Publication date |
---|---|
JP2001524120A (ja) | 2001-11-27 |
US6310202B1 (en) | 2001-10-30 |
FR2762992B1 (fr) | 2000-08-25 |
AU7536398A (en) | 1998-11-27 |
CA2287981A1 (fr) | 1998-11-12 |
EP0983283A1 (fr) | 2000-03-08 |
FR2762992A1 (fr) | 1998-11-13 |
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