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12/29/05 - USPTO Class 514 | 100 views | #20050288324 | Prev - Next | About this Page

Aromatic sulfonamides as peroxynitrite-rearrangement catalysts

Title: Aromatic sulfonamides as peroxynitrite-rearrangement catalysts

Related Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Designated Organic Active Ingredient Containing (doai), Heterocyclic Carbon Compounds Containing A Hetero Ring Having Chalcogen (i.e., O,s,se Or Te) Or Nitrogen As The Only Ring Hetero Atoms Doai, Hetero Ring Is Six-membered Consisting Of One Nitrogen And Five Carbon Atoms, Polycyclo Ring System Having The Six-membered Hetero Ring As One Of The Cyclos, Bicyclo Ring System Having The Six-membered Hetero Ring As One Of The Cyclos, Isoquinolines (including Hydrogenated)

Brief Patent Description - Full Patent Description - Patent Claims

The Patent Description & Claims data below is from USPTO Patent Application 20050288324, Aromatic sulfonamides as peroxynitrite-rearrangement catalysts.

1. A compound of formula I 15in which A) R.sup.1 is a C.sub.5-C.sub.6-alkylene-containing ring which may optionally be substituted one or more times by C.sub.1-C.sub.6-alkyl and which ring may optionally be interrupted by one or more nitrogen, sulfur or oxygen atoms and/or may contain one or more possible double bonds in the ring, or is a C.sub.3-C.sub.7-aryl or C.sub.3-C.sub.12-heteroaryl, which may optionally be substituted one or more times, identically or differently, by halogen, hydroxyl, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, R.sup.2 and R.sup.3 are each, independently of one another, C.sub.2-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, hydroxyl, nitro, halogen, C.sub.1-C.sub.6-alkyl, COOH, CF.sub.3 or C.sub.1-C.sub.6-alkoxy, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof, wherein the compound of formula I is not 16or B) R.sup.1 is a C.sub.5-C.sub.6-alkylene-containing ring which may optionally be substituted one or more times by C.sub.1-C.sub.6-alkyl and which ring may optionally be interrupted by one or more nitrogen, sulfur or oxygen atoms and/or may contain one or more possible double bonds in the ring, or is a C.sub.3-C.sub.7-aryl or C.sub.3-C.sub.12-heteroaryl, which may optionally be substituted one or more times, identically or differently by halogen, hydroxyl, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, wherein R.sup.1 is not 17R.sup.2 and R.sup.3 are each, independently of one another. C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, hydroxyl, nitro, halogen, C.sub.1-C.sub.6-akyl, COOH, CF.sub.3 or C.sub.1-C.sub.6-alkoxy. or an the isomer, diastereomer, enantiomer thereof, or a salt thereof, or C) R.sup.1 is a C.sub.5-C.sub.6-alkylene-containing ring which may optionally be substituted one or more times by C.sub.1-C.sub.6-alkyl and which ring may optionally be interrupted by one or more nitrogen, sulfur or oxygen atoms and/or may contain one or more possible double bonds in the ring, or is a C.sub.3-C.sub.7-aryl or C.sub.3-C.sub.12-heteroaryl, which may optionally be substituted one or more times, identically or differently, by halogen, hydroxyl, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, R.sup.2 and R.sup.3 are each, independently of one another, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, or R.sup.2 and R.sup.3 form a C.sub.5-alkylene-containing ring together with the nitrogen atom, which may optionally be interrupted by a further nitrogen atom in the ring, and which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, hydroxyl, nitro, halogen, C.sub.1-C.sub.6-alkyl, COOH, CF.sub.3 or C.sub.1-C.sub.6-alkoxy, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof; or D) R.sup.1 is 18R.sup.2 and R.sup.3 are each, independently of one another, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be interrupted by a further nitrogen atom in the ring, and which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, hydroxyl, nitro, halogen, C.sub.1-C.sub.6-alkyl, COOH, CF.sub.3 or C.sub.1-C.sub.6-alkoxy, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

2. A compound of formula I according to claim 1, in which in A) R.sup.1 is a C.sub.5-C.sub.6-alkylene-containing ring which may optionally be substituted one or more times by methyl, and which ring may optionally be interrupted by one or more nitrogen, sulfur or oxygen atoms and/or one or more possible double bonds may be present in the ring, or is a C.sub.3-C.sub.6-aryl or C.sub.3-C.sub.12-heteroaryl, R.sup.2 and R.sup.3 are each, independently of one another, C.sub.2-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

3. A compound of formula I according to claim 1, in which in A) R.sup.1 is 19R.sup.2 and R.sup.3 are each, independently of one another, C.sub.2-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.2-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer. enantiomer thereof, or a salt thereof.

4. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of formula I 20in which R.sup.1 is a C.sub.1-C.sub.6-alkyl, R.sup.2 and R.sup.3 are each, independently of one another, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be interrupted by a further nitrogen atom in the ring, and which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, hydroxyl, nitro, halogen, C.sub.1-C.sub.6-alkyl, COOH, CF.sub.3 or C.sub.1-C.sub.6-alkoxy, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

5. A method for the treatment or prophylaxis of a chronic or acute neurodegenerative disorder, an autoimmune disease, an inflammatory disorder, an infectious disease, cancer, a viral infection, a cardiovascular disorder, or a nephrological disorder comprising administering to a patient in need thereof an effective amount of a pharmaceutical composition comprising a pharmaceutically acceptable carrier and an effective amount of a compound according to claim 1.

6. A method according to claim 5, which is for the treatment or prophylaxis of Huntington's disease, amyotrophic lateral sclerosis, Parkinson's disease, dementia, Alzheimer's disease, HIV dementia, presenile dementia, Korksakoff's disease, epilepsy, schizophrenia, depression, cerebral ischemia, neurotrauma, hypotension, adult respiratory distress syndrome, sepsis, septic shock, rheumatoid arthritis, osteoarthritis, inflammatory disease of the pelvis/bowel, bowel disease, meningitis, multiple sclerosis, alopecia, psoriasis, a disease caused by a unicellular parasite a solid tumor, leukemia, a cytomegalovirus infection, hepatitis, hepatitis B or C, an HIV disorder, ischemic reperfusion disorder, stenoses, arterioscleroses, restenoses, or glomerulonephritis.

7-9. (canceled)

10. A method for catalyzing peroxynitrite rearrangement comprising administering to a patient in need thereof an effective amount of a pharmaceutical composition comprising a pharmaceutically acceptable carrier and an effective amount of a compound according to claim 1.

11-12. (canceled)

13. A compound of formula I according to claim 1, wherein in D) R.sup.1 is 21

14. A compound of formula I according to claim 1, wherein in B) R.sup.1 is a C.sub.5-C.sub.6-alkylene-containing ring which may optionally be substituted one or more times by methyl, and which ring may optionally be interrupted by one or more nitrogen, sulfur or oxygen atoms and/or one or more possible double bonds may be present in the ring, or is a C.sub.3-C.sub.6-aryl or C.sub.3-C.sub.12-heteroaryl, R.sup.2 and R.sup.3 are each, independently of one another, C.sub.1-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

15. A compound of formula I according to claim 1, wherein in B) R.sup.1 is 22R.sup.2 and R.sup.3 are each, independently of one another, C.sub.1-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

16. A compound of formula I according to claim 1, wherein in C) R.sup.1 is a C.sub.5-C.sub.6-alkylene-containing ring which may optionally be substituted one or more times by methyl, and which ring may optionally be interrupted by one or more nitrogen, sulfur or oxygen atoms and/or one or more possible double bonds may be present in the ring, or is a C.sub.3-C.sub.6-aryl or C.sub.3-C.sub.12-heteroaryl, R.sup.2 and R.sup.3 are each, independently of one another, C.sub.2-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.5-alkylene-containing ring together with the nitrogen atom, which may optionally be interrupted by a further nitrogen atom in the ring, and which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

17. A compound of formula I according to claim 1, wherein in C) R.sup.1 is 23R.sup.2 and R.sup.3 are each, independently of one another, C.sub.2-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.5-alkylene-containing ring together with the nitrogen atom, which may optionally be interrupted by a further nitrogen atom in the ring, and which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof

18. A compound of formula I according to claim 1, wherein in D) R.sup.2 and R.sup.3 are each, independently of one another, C.sub.1-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be interrupted by a further nitrogen atom in the ring, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

19. A compound of formula I according to claim 1, wherein in D) R.sup.2 and R.sup.3 are each, independently of one another, C.sub.1-C.sub.6-alkyl, or R.sup.2 and R.sup.3 form a C.sub.5-C.sub.6-alkylene-containing ring together with the nitrogen atom, which may optionally be interrupted by a further nitrogen atom in the ring, which may optionally be substituted by C.sub.1-C.sub.4-alkyl, and R.sup.4 is hydrogen, CF.sub.3, --O--CH.sub.3 or nitro, or an the isomer, diastereomer, enantiomer thereof, or a salt thereof.

20. A compound of formula I according to claim 15, which is thiophene-2-sulfonic acid 4-dimethylamino-2-nitrophenylamide; or 3,5-dimethylisoxazole-4-sulfonic acid 4-dimethylamino-2-nitrophenylamide.

21. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of claim 1.

22. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of claim 20.

Brief Patent Description - Full Patent Description - Patent Claims

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