RU97113367A - DERIVATIVES OF NEURAMINIC ACID, THEIR PRODUCTION AND APPLICATION IN MEDICINE - Google Patents
DERIVATIVES OF NEURAMINIC ACID, THEIR PRODUCTION AND APPLICATION IN MEDICINEInfo
- Publication number
- RU97113367A RU97113367A RU97113367/04A RU97113367A RU97113367A RU 97113367 A RU97113367 A RU 97113367A RU 97113367/04 A RU97113367/04 A RU 97113367/04A RU 97113367 A RU97113367 A RU 97113367A RU 97113367 A RU97113367 A RU 97113367A
- Authority
- RU
- Russia
- Prior art keywords
- group
- carbon atoms
- compound according
- hydrogen atom
- atom
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- CERZMXAJYMMUDR-QBTAGHCHSA-N 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid Chemical class N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO CERZMXAJYMMUDR-QBTAGHCHSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 22
- 125000004432 carbon atoms Chemical group C* 0.000 claims 18
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 11
- 125000003277 amino group Chemical group 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 8
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims 6
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims 6
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 2
- 102000005348 Neuraminidase Human genes 0.000 claims 2
- 108010006232 Neuraminidase Proteins 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 201000009910 diseases by infectious agent Diseases 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
Claims (27)
где R1 представляет алкильную группу, имеющую от 1 до 4 углеродных атомов, или галоалкильную группу, имеющую от 1 до 4 углеродных атомов;
R2 и R3 являются одинаковыми или отличными друг от друга и, каждый, представляет атом водорода или алифатическую ацильную группу, имеющую от 2 до 25 углеродных атомов;
Х представляет гидрокси группу, атом галогена, алкокси группу, имеющую от 1 до 4 углеродных атомов, или группу формулы RaO-, где Ra представляет алифатическую ацильную группу, имеющую от 2 до 25 углеродных атомов;
Y представляет группу формулы RbRcN- или RbRcN-O-, где Rb и Rc являются одинаковыми или отличными друг от друга и, каждый представляет атом водорода или алкильную группу, имеющую от 1 до 4 углеродных атомов;
Z представляет атом кислорода или атом серы;
при условии, что когда Y представляет амино группу и Z представляет атом кислорода, тогда Х представляет атом галогена или алкокси группу;
и их фармацевтически приемлемые соли и их сложные эфиры.1. Compounds of the formula
where R 1 represents an alkyl group having from 1 to 4 carbon atoms, or a haloalkyl group having from 1 to 4 carbon atoms;
R 2 and R 3 are the same or different from each other and each represents a hydrogen atom or an aliphatic acyl group having from 2 to 25 carbon atoms;
X represents a hydroxy group, a halogen atom, an alkoxy group having from 1 to 4 carbon atoms, or a group of the formula R a O—, where R a represents an aliphatic acyl group having from 2 to 25 carbon atoms;
Y represents a group of the formula R b R c N— or R b R c NO—, where R b and R c are the same or different from each other and each represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
Z represents an oxygen atom or a sulfur atom;
with the proviso that when Y represents an amino group and Z represents an oxygen atom, then X represents a halogen atom or an alkoxy group;
and their pharmaceutically acceptable salts and their esters.
5-ацетамидо-4-гуанидино-2, 3, 4, 5, 7-пентадезокси-7-фторо-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-9-O-додеканоил-2,3,4,5,7-пентадезокси-7-фторо-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-9-O-миристоил-2,3,4,5,7-пентадезокси-7-фторо-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-aцeтaмидo-4-гуaнидинo-9-O-пaльмитoил-2,3,4,5,7-пентадезокси-7-фторо-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-2, 3, 4, 5, 7-пентадезокси-7-метокси-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-9-O-миристоил-2,3,4,5,7-пентадезокси-7-метокси-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-2, 3, 4, 5, 7-пентадезокси-7-этокси-глицеро-галакто-нон-2-енопиранозоевая кислоту,
5-ацетамидо-4-гуанидино-9-O-октаноил-2,3,4,5,7-пентадезокси-7-этокси-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-9-O-додеканоил-2,3,4,5,7-пентадезокси-7-этокси-глицеро-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-9-O-миристоил-2,3,4,5,7-пентадезокси-7-этокси-глицерo-галакто-нон-2-енопиранозоевая кислоту;
5-ацетамидо-4-гуанидино-9-O-пальмитоил-2,3,4,5,7-пентадезокси-7-этокси-глицеро-галакто-нон-2-енопиранозоевая кислоту,
и их фармацевтически приемлемые соли и их сложные эфиры.25. The compound according to claim 1, which is:
5-acetamido-4-guanidino-2, 3, 4, 5, 7-pentadeoxy-7-fluoro- glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-9-O-dodecanoyl-2,3,4,5,7-pentadeoxy-7-fluoro- glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-9-O-myristoyl-2,3,4,5,7-pentadeoxy-7-fluoro- glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-9-O-palmitoyl-2,3,4,5,7-pentadeoxy-7-fluoro- glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-2, 3, 4, 5, 7-pentadeoxy-7-methoxy glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-9-O-myristoyl-2,3,4,5,7-pentadeoxy-7-methoxy glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-2, 3, 4, 5, 7-pentadeoxy-7-ethoxy- glycerol galacto-non-2-enopyranosoic acid,
5-acetamido-4-guanidino-9-O-octanoyl-2,3,4,5,7-pentadeoxy-7-ethoxy- glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-9-O-dodecanoyl-2,3,4,5,7-pentadeoxy-7-ethoxy- glycerol galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-9-O-myristoyl-2,3,4,5,7-pentadeoxy-7-ethoxy- glycero- galacto-non-2-enopyranosoic acid;
5-acetamido-4-guanidino-9-O-palmitoyl-2,3,4,5,7-pentadeoxy-7-ethoxy- glycerol galacto-non-2-enopyranosoic acid,
and their pharmaceutically acceptable salts and their esters.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8-191862 | 1996-07-22 | ||
JP19186296 | 1996-07-22 | ||
JP8688897 | 1997-04-04 | ||
JP9-86888 | 1997-04-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2124509C1 RU2124509C1 (en) | 1999-01-10 |
RU97113367A true RU97113367A (en) | 1999-07-10 |
Family
ID=26427962
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU97113367A RU2124509C1 (en) | 1996-07-22 | 1997-07-21 | Neuraminic acid derivatives or their pharmaceutically acceptable salts, or their esters and a pharmaceutical composition exhibiting sialidase-inhibiting activity |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP0823428B1 (en) |
KR (1) | KR100506578B1 (en) |
CN (1) | CN1127494C (en) |
AT (1) | ATE211468T1 (en) |
AU (1) | AU700926B2 (en) |
CA (1) | CA2210492C (en) |
CZ (1) | CZ291960B6 (en) |
DE (1) | DE69709795T2 (en) |
DK (1) | DK0823428T3 (en) |
ES (1) | ES2167682T3 (en) |
HK (1) | HK1007879A1 (en) |
HU (1) | HU223494B1 (en) |
ID (1) | ID17474A (en) |
IL (1) | IL121305A (en) |
MX (1) | MX9705559A (en) |
NO (1) | NO317704B1 (en) |
NZ (1) | NZ328353A (en) |
PT (1) | PT823428E (en) |
RU (1) | RU2124509C1 (en) |
TW (1) | TW418200B (en) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6451766B1 (en) | 1996-07-22 | 2002-09-17 | Sankyo Company, Limited | Neuraminic acid derivatives, their preparation and their medical use |
US6340702B1 (en) | 1996-07-22 | 2002-01-22 | Sankyo Company, Limited | Neuraminic acid derivatives, their preparation and their medical use |
US6518305B1 (en) | 1998-04-23 | 2003-02-11 | Abbott Laboratories | Five-membered carbocyclic and heterocyclic inhibitors of neuraminidases |
US6455571B1 (en) | 1998-04-23 | 2002-09-24 | Abbott Laboratories | Inhibitors of neuraminidases |
US6593314B1 (en) | 1999-10-19 | 2003-07-15 | Abbott Laboratories | Neuraminidase inhibitors |
TWI291462B (en) * | 2000-04-25 | 2007-12-21 | Daiichi Sankyo Co Ltd | Hydrate crystal of neuraminic acid compound |
FR2809104B1 (en) * | 2000-05-19 | 2002-08-02 | Univ Paris Curie | PROCESS FOR THE TREATMENT OF PLANT MATERIAL, COMPOSITIONS COMPRISING D-DERIVATIVES OF THE N-ACYLGLUCOSAMINE TYPE, USE OF SUCH COMPOUNDS AS BIO-PROTECTIVE AGENTS, AND TREATED PLANT MATERIAL. |
WO2001087876A1 (en) * | 2000-05-19 | 2001-11-22 | Sankyo Company, Limited | Sialic acid derivatives |
AUPR001000A0 (en) | 2000-09-08 | 2000-10-05 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
WO2002076980A1 (en) * | 2001-03-27 | 2002-10-03 | Sankyo Company, Limited | Sialic acid derivatives |
WO2002092555A1 (en) * | 2001-05-11 | 2002-11-21 | Sankyo Company, Limited | Sialic acid derivatives |
DK2123271T3 (en) * | 2007-03-07 | 2012-01-23 | Daiichi Sankyo Co Ltd | Medication for the treatment of influenza |
TWI546306B (en) * | 2007-04-11 | 2016-08-21 | 第一三共股份有限公司 | Method for manufacturing neuraminic acid derivatives |
KR100930963B1 (en) * | 2008-02-26 | 2009-12-11 | 한국기계연구원 | Expansion valve for air conditioner using stacked piezoelectric pilot valve |
JP2012510456A (en) * | 2008-11-28 | 2012-05-10 | シプラ・リミテッド | Process for producing zanamivir and intermediate for use in the process |
TWI491416B (en) | 2008-12-24 | 2015-07-11 | Daiichi Sankyo Co Ltd | A dry powder pharmaceutical composition for inhalation |
BRPI1010981A2 (en) | 2009-05-15 | 2018-12-04 | Redx Pharma Ltd | "redox drug derivatives" |
CN102532080A (en) * | 2010-12-29 | 2012-07-04 | 中国科学院上海药物研究所 | Novel sialic acid derivant, preparation method thereof, drug composite comprising the same and application thereof |
CA2859296C (en) * | 2011-12-16 | 2016-10-11 | Daiichi Sankyo Company, Limited | Method for manufacturing neuraminic acid derivatives |
CN104418876B (en) * | 2013-09-09 | 2019-05-17 | 中国科学院上海有机化学研究所 | The intermediate and its synthetic method of zanamivir and La Na meter Wei |
CN114843564B (en) * | 2022-03-28 | 2023-08-25 | 电子科技大学 | Cathode-anode co-doped solid oxide battery oxygen electrode material and preparation method thereof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SK282950B6 (en) * | 1990-04-24 | 2003-01-09 | Biota Scientific Management Pty Ltd | Alpha-D-neuraminic acid derivatives, their preparation method, use and pharmaceutical preparations based on them |
CA2081068C (en) * | 1991-10-23 | 2005-11-29 | Laurence Mark Von Itzstein | Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of .alpha.-d-neuraminic acid |
GB9325841D0 (en) * | 1993-12-17 | 1994-02-23 | Glaxo Group Ltd | Chemical compounds |
GB9400206D0 (en) * | 1994-01-07 | 1994-03-02 | Glaxo Group Ltd | Chemical compound |
AUPM354694A0 (en) * | 1994-01-27 | 1994-02-17 | Biota Scientific Management Pty Ltd | Chemical compounds |
GB9516276D0 (en) * | 1995-08-08 | 1995-10-11 | Biota Scient Management | Chemical compounds |
-
1997
- 1997-07-11 DE DE69709795T patent/DE69709795T2/en not_active Expired - Lifetime
- 1997-07-11 DK DK97305159T patent/DK0823428T3/en active
- 1997-07-11 EP EP97305159A patent/EP0823428B1/en not_active Expired - Lifetime
- 1997-07-11 PT PT97305159T patent/PT823428E/en unknown
- 1997-07-11 AT AT97305159T patent/ATE211468T1/en active
- 1997-07-11 ES ES97305159T patent/ES2167682T3/en not_active Expired - Lifetime
- 1997-07-14 IL IL12130597A patent/IL121305A/en not_active IP Right Cessation
- 1997-07-15 CA CA002210492A patent/CA2210492C/en not_active Expired - Lifetime
- 1997-07-16 AU AU28662/97A patent/AU700926B2/en not_active Expired
- 1997-07-16 NZ NZ328353A patent/NZ328353A/en not_active IP Right Cessation
- 1997-07-21 NO NO19973363A patent/NO317704B1/en not_active IP Right Cessation
- 1997-07-21 CZ CZ19972316A patent/CZ291960B6/en not_active IP Right Cessation
- 1997-07-21 RU RU97113367A patent/RU2124509C1/en active
- 1997-07-21 ID IDP972509A patent/ID17474A/en unknown
- 1997-07-21 TW TW086110312A patent/TW418200B/en not_active IP Right Cessation
- 1997-07-22 KR KR1019970034213A patent/KR100506578B1/en not_active IP Right Cessation
- 1997-07-22 MX MX9705559A patent/MX9705559A/en unknown
- 1997-07-22 HU HU9701270A patent/HU223494B1/en active IP Right Grant
- 1997-07-22 CN CN97117883A patent/CN1127494C/en not_active Expired - Lifetime
-
1998
- 1998-06-25 HK HK98106680A patent/HK1007879A1/en not_active IP Right Cessation
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