RU99100377A - NEW AROMATIC DERIVATIVES, FILLED WITH RIBOSE, METHOD OF THEIR PRODUCTION AND THEIR APPLICATION AS A MEDICINE - Google Patents
NEW AROMATIC DERIVATIVES, FILLED WITH RIBOSE, METHOD OF THEIR PRODUCTION AND THEIR APPLICATION AS A MEDICINEInfo
- Publication number
- RU99100377A RU99100377A RU99100377/04A RU99100377A RU99100377A RU 99100377 A RU99100377 A RU 99100377A RU 99100377/04 A RU99100377/04 A RU 99100377/04A RU 99100377 A RU99100377 A RU 99100377A RU 99100377 A RU99100377 A RU 99100377A
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- RU
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- Prior art keywords
- radical
- methyl
- denotes
- formula
- compounds
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- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000003254 radicals Chemical class 0.000 claims 19
- -1 alkynyl radical Chemical class 0.000 claims 16
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 14
- 125000004432 carbon atoms Chemical group C* 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 150000002829 nitrogen Chemical group 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 7
- UFYABCWJPZTWHA-UHFFFAOYSA-M 5-methyl-1H-pyrrole-2-carboxylate Chemical compound CC1=CC=C(C([O-])=O)N1 UFYABCWJPZTWHA-UHFFFAOYSA-M 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl radical Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 5
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N Methyl radical Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 2
- 230000000903 blocking Effects 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drugs Drugs 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 125000004434 sulfur atoms Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Claims (1)
в которой R1 обозначает атом водорода, гидроксильный радикал, алкильный, алкенильный или алкинильный радикал, необязательно прерванный атомом кислорода, серы или азота, содержащий до 12 атомов углерода, линейный, разветвленный или циклический, необязательно замещенный одним или несколькими атомами галогена, одним или несколькими радикалами в котором Rа и Rb, одинаковые или разные, обозначают атом водорода, алкильный радикал, содержащий до 8 атомов углерода, или Rа и Rb образуют с атомом азота, с которым они связаны, гетероцикл, необязательно содержащий другой гетероатом, выбираемый среди азота, серы или кислорода,
или R1 обозначает алкоксильный радикал, содержащий до 8 атомов углерода, необязательно замещенный одним или несколькими заместителями из указанных выше,
или R1 обозначает радикал NRсRd, в котором Rс и Rd, одинаковые или разные, обозначают атом водорода или алкильный радикал, содержащий до 12 атомов углерода, необязательно замещенный одним или несколькими заместителями из указанных выше, или Rс и Rd образуют вместе с атомом азота, с которым они связаны, гетероцикл, необязательно содержащий другой гетероатом, выбираемый среди азота, серы или кислорода,
Х обозначает атом кислорода, или радикал N-Nalс1, или NОalс2, в котором alс1 и alс2 обозначают алкильный радикал, необязательно прерванный атомом кислорода, серы или азота, содержащий до 12 атомов углерода, необязательно замещенный одним или несколькими атомами галогена, одним или несколькими радикалами в которых Rе и Rf, одинаковые или отличающиеся друг от друга, обозначают атом водорода, алкильный радикал, содержащий до 8 атомов углерода, необязательно замещенный, или Rе и Rf могут образовывать вместе с атомом азота, с которым они связаны, гетероцикл, который может содержать, кроме того, атом кислорода, серы и другой атом азота,
R2 обозначает атом водорода или атом галогена,
R3 обозначает атом водорода, алкильный радикал, содержащий до 8 атомов углерода, или атом галогена,
R4 обозначает радикал в котором Rg и Rh, одинаковые или отличающиеся друг от друга, обозначают атом водорода, алкильный радикал, линейный, разветвленный или циклический, содержащий до 8 атомов углерода, арильный или гетероарильный радикал, необязательно замещенный, или Rg и Rh образуют с атомом азота, с которым они связаны, гетероцикл, который может содержать, кроме того, атом кислорода, серы и другой атом азота,
или R4 обозначает арильный или гетероарильный радикал, необязательно замещенный одним или несколькими атомами галогена, одним или несколькими гидроксильными радикалами, одним или нескольким алкильными или алкоксильными радикалами, содержащими до 8 атомов углерода,
R5 обозначает атом водорода, радикал О-алкил, содержащий до 4 атомов углерода,
R6 обозначает радикал алкил или СН2-О-алкил, в котором алкил обозначает алкильный радикал, содержащий до 8 атомов углерода,
R7 обозначает атом водорода или алкильный радикал, содержащий до 8 атомов углерода, также как соли соединений формулы (I).1. The compounds of formula (I):
in which R 1 denotes a hydrogen atom, a hydroxyl radical, an alkyl, alkenyl or alkynyl radical optionally interrupted by an oxygen, sulfur or nitrogen atom containing up to 12 carbon atoms, linear, branched or cyclic, optionally substituted by one or more halogen atoms, one or more radicals in which R a and R b are the same or different, represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or R a and R b form with the nitrogen atom to which they are bound, a heterocycle, optionally containing another heteroatom, chosen among nitrogen, sulfur or oxygen,
or R 1 denotes a CNS radical containing up to 8 carbon atoms, optionally substituted by one or more of the substituents indicated above,
or R 1 denotes an NR radical with R d in which R c and R d are the same or different, denote a hydrogen atom or an alkyl radical containing up to 12 carbon atoms, optionally substituted with one or more of the substituents indicated above, or R c and R d form, together with the nitrogen atom to which they are linked, a heterocycle, optionally containing another heteroatom, selected among nitrogen, sulfur or oxygen,
X represents an oxygen atom, or an N-Nalc 1 , or NOalc 2 radical, in which alc 1 and alc 2 denote an alkyl radical, optionally interrupted by an oxygen, sulfur or nitrogen atom containing up to 12 carbon atoms, optionally substituted by one or more halogen atoms, one or more radicals in which R e and R f identical or different from each other, denote a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, optionally substituted, or R e and R f can form together with the nitrogen atom to which they are bound, a heterocycle which may contain, in addition, an oxygen atom, sulfur and another nitrogen atom,
R 2 denotes a hydrogen atom or a halogen atom,
R 3 denotes a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or a halogen atom,
R 4 denotes a radical in which R g and R h , the same or different from each other, represent a hydrogen atom, an alkyl radical, linear, branched or cyclic, containing up to 8 carbon atoms, aryl or heteroaryl radical, optionally substituted, or R g and R h form with the nitrogen atom to which they are linked, a heterocycle, which may contain, in addition, an oxygen atom, sulfur and another nitrogen atom,
or R 4 denotes an aryl or heteroaryl radical, optionally substituted by one or more halogen atoms, one or more hydroxyl radicals, one or more alkyl or alkoxy radicals containing up to 8 carbon atoms,
R 5 denotes a hydrogen atom, an O-alkyl radical containing up to 4 carbon atoms,
R 6 denotes an alkyl radical or CH 2 -O-alkyl, in which alkyl denotes an alkyl radical containing up to 8 carbon atoms,
R 7 denotes a hydrogen atom or an alkyl radical containing up to 8 carbon atoms, as well as salts of the compounds of formula (I).
8. Соединения формулы (I) по любому из пп.1 - 6, в которых R4 обозначает радикал NН-циклопропил.7. The compounds of formula (I) according to any one of paragraphs.1 - 6, in which R 4 denotes a radical
8. The compounds of formula (I) according to any one of paragraphs.1 - 6, in which R 4 denotes the radical NN-cyclopropyl.
14. Соединения формулы (I) по п.13, в которых R1 представляет собой радикал метил или О-этил.13. The compounds of formula (I) according to claim 12, in which R 1 is a CH 3 radical,
14. The compounds of formula (I) according to claim 13, in which R 1 is a methyl or O-ethyl radical.
3'-[5-метил-1Н-пиррол-2-карбоксилат] 3-ацетил-7-((6-дезокси-5-С-метил-4-О-метил-альфа-L-ликсо-гексопиранозил)-окси)-4-гидрокси-8-метил-2Н-1-бензопиран-2-она,
3'-[5-метил-1Н-пиррол-2-карбоксилат] 7-((6-дезокси-5-С-метил-4-О-метил-альфа-L-ликсо-гексопиранозил)окси)-4-гидрокси-8-метил-2-оксо-2Н-1-бензопиран-3-этилкарбоксилата,
3'-[5-метил-1Н-пиррол-2-карбоксилат] 7-((6-дезокси-5-С-метил-4-О-метил-альфа-L-ликсо-гексопиранозил)окси)-4-гидрокси-3-(1-метоксиимино)этил)-8-метил-2Н-1-бензопиран-2-она,
3'-[5-метил-1Н-пиррол-2-карбоксилат] 7-((6-дезокси-5-С-метил-4-О-метил-альфа-L-ликсо-гексопиранозил)окси)-3-(этоксиацетил)-4-гидрокси-8-метил-2Н-1-бензопиран-2-она,
3'-[5-метил-1Н-пиррол-2-карбоксилат] 3-(циклопропилкарбонил)-7-((6-дезокси-5-С-метил-4-О-метил-альфа-L-ликсо-гексопиранозил)окси)-4-гидрокси-8-метил-2Н-1-бензопиран-2-она,
3'-[5-метил-1Н-пиррол-2-карбоксилат] 7-((6-дезокси-5-С-метил-4-О-метил-альфа-L-ликсо-гексопиранозил)окси)-4-гидрокси-8-метил-2Н-1-бензопиран-3-карбоксамида.15. The compounds of formula (I), the names of which follow:
3 '- [5-methyl-1H-pyrrole-2-carboxylate] 3-acetyl-7 - ((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lix-hexopyranosyl) -oxy ) -4-hydroxy-8-methyl-2H-1-benzopyran-2-one,
3 '- [5-methyl-1H-pyrrole-2-carboxylate] 7 - ((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lixo-hexopyranosyl) oxy) -4-hydroxy -8-methyl-2-oxo-2H-1-benzopyran-3-ethylcarboxylate,
3 '- [5-methyl-1H-pyrrole-2-carboxylate] 7 - ((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lixo-hexopyranosyl) oxy) -4-hydroxy -3- (1-methoxyimino) ethyl) -8-methyl-2H-1-benzopyran-2-one,
3 '- [5-methyl-1H-pyrrole-2-carboxylate] 7 - ((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lixo-hexopyranosyl) oxy) -3- ( ethoxyacetyl) -4-hydroxy-8-methyl-2H-1-benzopyran-2-one,
3 '- [5-methyl-1H-pyrrole-2-carboxylate] 3- (cyclopropylcarbonyl) -7 - ((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lixo-hexopyranosyl) oxy) -4-hydroxy-8-methyl-2H-1-benzopyran-2-one,
3 '- [5-methyl-1H-pyrrole-2-carboxylate] 7 - ((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lixo-hexopyranosyl) oxy) -4-hydroxy -8-methyl-2H-1-benzopyran-3-carboxamide.
в которых заместители сохраняют то же самое значение, что в п.1, отличающийся тем, что соединение формулы (II):
в которой R8 обозначает свободный или блокированный гидроксильный радикал,
Z обозначает атом водорода или радикал
Х, R1, R2 и R3 сохраняют их предыдущее значение, ОR9 обозначает свободный или блокированный гидроксильный радикал,
подвергают воздействию соединения формулы (III):
в которой R5, R6 и R7 сохраняют их предыдущее значение, ОR'4 обозначает блокированный гидроксильный радикал, R''4 обозначает атом водорода, или, лучше, R'4 и R''4 образуют вместе с атомами углерода, с которыми они связаны, цикл
чтобы получить соединение формулы (IV):
в которой заместители сохраняют их предыдущее значение, затем полученное таким образом соединение формулы (IV) подвергают следующим стадиям, в совокупности или частично:
отщепление гидроксила в положении 4 после возможного блокирования гидроксила сахара в α-положении ОR'4,
если Z является атомом водорода, введению радикала после возможного блокирования реакционноспособных гидроксильных групп,
введению радикала путем замещения этого радикала радикалом R'4,
модификации радикала Х.16 A method of obtaining compounds of formula (I), such as defined in any of paragraphs.1 - 15,
in which the substituents retain the same value as in claim 1, characterized in that the compound of formula (II):
in which R 8 denotes a free or blocked hydroxyl radical,
Z represents a hydrogen atom or a radical
X, R 1 , R 2 and R 3 retain their previous value, OR 9 denotes a free or blocked hydroxyl radical,
exposed to compounds of formula (III):
in which R 5 , R 6 and R 7 retain their previous meaning, OR ′ 4 denotes a blocked hydroxyl radical, R ″ 4 denotes a hydrogen atom, or, better, R ′ 4 and R ″ 4 form together with carbon atoms, with which they are related, the cycle
to obtain the compound of formula (IV):
in which the substituents retain their previous value, then the compound of formula (IV) thus obtained is subjected to the following stages, in whole or in part:
cleavage of hydroxyl in position 4 after the possible blocking of the hydroxyl sugar in the α-position OR ' 4 ,
if Z is a hydrogen atom, the introduction of a radical after possible blocking of reactive hydroxyl groups,
the introduction of the radical by replacing this radical with the radical R ' 4 ,
modifications of radical X.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR96/07207 | 1996-06-11 | ||
FR9607207A FR2749585B1 (en) | 1996-06-11 | 1996-06-11 | NOVEL AROMATIC DERIVATIVES SUBSTITUTED BY RIBOSIS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS |
Publications (2)
Publication Number | Publication Date |
---|---|
RU99100377A true RU99100377A (en) | 2001-01-20 |
RU2194052C2 RU2194052C2 (en) | 2002-12-10 |
Family
ID=9492918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU99100377/04A RU2194052C2 (en) | 1996-06-11 | 1997-06-10 | Derivatives of benzopyrane-2-one, method of their synthesis, pharmaceutical composition comprising thereof and intermediate compounds |
Country Status (24)
Country | Link |
---|---|
US (2) | US6350733B1 (en) |
EP (1) | EP0906326B1 (en) |
JP (1) | JP2000511920A (en) |
CN (1) | CN1308342C (en) |
AR (1) | AR008228A1 (en) |
AT (1) | ATE209212T1 (en) |
AU (1) | AU712665B2 (en) |
BR (1) | BR9709676A (en) |
CA (1) | CA2258152C (en) |
CZ (1) | CZ296204B6 (en) |
DE (1) | DE69709732T2 (en) |
DK (1) | DK0906326T3 (en) |
ES (1) | ES2165067T3 (en) |
FR (1) | FR2749585B1 (en) |
HU (1) | HU222787B1 (en) |
IL (3) | IL127133A0 (en) |
NO (1) | NO313638B1 (en) |
PL (1) | PL187204B1 (en) |
PT (1) | PT906326E (en) |
RU (1) | RU2194052C2 (en) |
TR (1) | TR199802555T2 (en) |
TW (1) | TW561159B (en) |
WO (1) | WO1997047634A1 (en) |
ZA (1) | ZA974840B (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002300839B2 (en) * | 1998-01-08 | 2004-04-29 | Novexel | Novel aromatic amides, preparation method and application as medicines |
FR2784681B1 (en) * | 1998-10-15 | 2003-01-17 | Hoechst Marion Roussel Inc | NEW AROMATIC AMIDES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
TW538046B (en) * | 1998-01-08 | 2003-06-21 | Hoechst Marion Roussel Inc | Aromatic amides having antiobiotic activities and the preparation processes, intermediates and pharmaceutical composition thereof |
FR2773369B1 (en) * | 1998-01-08 | 2001-02-16 | Hoechst Marion Roussel Inc | NEW AROMATIC AMIDES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
FR2844273B1 (en) * | 2002-09-05 | 2008-04-04 | Aventis Pharma Sa | NOVEL HETEROCYCLIC COMPOUNDS, METHOD AND INTERMEDIARY PREPARATION AND USE AS MEDICAMENT, IN PARTICULAR AS INHIBITORS OF BETA-LACTAMASES AND ANTI-BACTERIALS. |
US7439253B2 (en) * | 2002-12-06 | 2008-10-21 | Novexel | Heterocyclic compounds, their preparation and their use as medicaments, in particular as antibacterials and beta-lactamase inhibitors |
KR101203124B1 (en) * | 2004-04-08 | 2012-11-20 | 아메데온, 인코포레이티드 | Materials and methods for treating coagulation disorders |
WO2007133211A1 (en) * | 2006-05-15 | 2007-11-22 | Xtl Biopharmaceuticals, Ltd. | 3,4-disubstituted coumarin and quinolone compounds |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4226978A (en) * | 1978-03-13 | 1980-10-07 | Miles Laboratories, Inc. | β-Galactosyl-umbelliferone-labeled aminoglycoside antibiotics and intermediates in their preparation |
CN1053193C (en) * | 1993-11-15 | 2000-06-07 | 吴羽化学工业株式会社 | Esculetin derivatives, process for manufacture and use thereof, and pharmaceutical composition |
TW538046B (en) * | 1998-01-08 | 2003-06-21 | Hoechst Marion Roussel Inc | Aromatic amides having antiobiotic activities and the preparation processes, intermediates and pharmaceutical composition thereof |
-
1996
- 1996-06-11 FR FR9607207A patent/FR2749585B1/en not_active Expired - Fee Related
-
1997
- 1997-06-02 ZA ZA974840A patent/ZA974840B/en unknown
- 1997-06-10 CN CNB971972257A patent/CN1308342C/en not_active Expired - Fee Related
- 1997-06-10 EP EP97928316A patent/EP0906326B1/en not_active Expired - Lifetime
- 1997-06-10 BR BR9709676-8A patent/BR9709676A/en not_active Application Discontinuation
- 1997-06-10 HU HU9902925A patent/HU222787B1/en not_active IP Right Cessation
- 1997-06-10 ES ES97928316T patent/ES2165067T3/en not_active Expired - Lifetime
- 1997-06-10 CA CA002258152A patent/CA2258152C/en not_active Expired - Fee Related
- 1997-06-10 IL IL12713397A patent/IL127133A0/en active IP Right Grant
- 1997-06-10 JP JP10501287A patent/JP2000511920A/en not_active Ceased
- 1997-06-10 US US09/202,218 patent/US6350733B1/en not_active Expired - Fee Related
- 1997-06-10 CZ CZ0406998A patent/CZ296204B6/en not_active IP Right Cessation
- 1997-06-10 AR ARP970102526A patent/AR008228A1/en active IP Right Grant
- 1997-06-10 WO PCT/FR1997/001022 patent/WO1997047634A1/en active IP Right Grant
- 1997-06-10 DK DK97928316T patent/DK0906326T3/en active
- 1997-06-10 AT AT97928316T patent/ATE209212T1/en not_active IP Right Cessation
- 1997-06-10 PT PT97928316T patent/PT906326E/en unknown
- 1997-06-10 PL PL97330550A patent/PL187204B1/en not_active IP Right Cessation
- 1997-06-10 TR TR1998/02555T patent/TR199802555T2/en unknown
- 1997-06-10 RU RU99100377/04A patent/RU2194052C2/en not_active IP Right Cessation
- 1997-06-10 AU AU32659/97A patent/AU712665B2/en not_active Ceased
- 1997-06-10 DE DE69709732T patent/DE69709732T2/en not_active Expired - Fee Related
- 1997-06-16 TW TW086108347A patent/TW561159B/en active
-
1998
- 1998-11-18 IL IL127133A patent/IL127133A/en not_active IP Right Cessation
- 1998-12-10 NO NO19985790A patent/NO313638B1/en unknown
-
2001
- 2001-06-07 US US09/875,860 patent/US6812331B2/en not_active Expired - Fee Related
- 2001-12-04 IL IL146925A patent/IL146925A/en not_active IP Right Cessation
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