UA61062C2 - Racemic and optically active trans apovincaminic acid ester derivatives - Google Patents
Racemic and optically active trans apovincaminic acid ester derivatives Download PDFInfo
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- UA61062C2 UA61062C2 UA98052781A UA98052781A UA61062C2 UA 61062 C2 UA61062 C2 UA 61062C2 UA 98052781 A UA98052781 A UA 98052781A UA 98052781 A UA98052781 A UA 98052781A UA 61062 C2 UA61062 C2 UA 61062C2
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- -1 apovincaminic acid ester Chemical class 0.000 title abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 39
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 80
- 238000002360 preparation method Methods 0.000 abstract description 24
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- 238000000034 method Methods 0.000 abstract description 20
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
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- 208000025966 Neurological disease Diseases 0.000 abstract 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 241001465754 Metazoa Species 0.000 description 5
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 5
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- 125000004494 ethyl ester group Chemical group 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 230000037361 pathway Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229950000628 silibinin Drugs 0.000 description 1
- 235000014899 silybin Nutrition 0.000 description 1
- CYGIJEJDYJOUAN-JSGXPVSSSA-N silydianin Chemical compound C1=C(O)C(OC)=CC([C@H]2[C@H]3C=C([C@@H]4[C@@](C3=O)(O)OC[C@@H]42)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 CYGIJEJDYJOUAN-JSGXPVSSSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960000744 vinpocetine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9503736A HU214600B (hu) | 1995-12-22 | 1995-12-22 | Transz-apovinkaminsav-észter-származékok, az azokat tartalmazó gyógyszerkészítmények és eljárás ezek előállítására |
| PCT/HU1996/000075 WO1997023481A1 (en) | 1995-12-22 | 1996-12-13 | Trans apovincaminic acid ester derivatives as drugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA61062C2 true UA61062C2 (en) | 2003-11-17 |
Family
ID=10987512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA98052781A UA61062C2 (en) | 1995-12-22 | 1996-12-13 | Racemic and optically active trans apovincaminic acid ester derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6093720A (pt) |
| EP (1) | EP0876367B1 (pt) |
| JP (1) | JP2000502676A (pt) |
| KR (1) | KR19990076606A (pt) |
| CN (1) | CN1072670C (pt) |
| AR (1) | AR005182A1 (pt) |
| AT (1) | ATE223914T1 (pt) |
| AU (1) | AU1166997A (pt) |
| CA (1) | CA2238635A1 (pt) |
| CZ (1) | CZ290383B6 (pt) |
| DE (1) | DE69623656T2 (pt) |
| DK (1) | DK0876367T3 (pt) |
| ES (1) | ES2181926T3 (pt) |
| HU (1) | HU214600B (pt) |
| IL (1) | IL124097A (pt) |
| PL (1) | PL186626B1 (pt) |
| PT (1) | PT876367E (pt) |
| RU (1) | RU2161157C2 (pt) |
| TW (1) | TW366348B (pt) |
| UA (1) | UA61062C2 (pt) |
| WO (1) | WO1997023481A1 (pt) |
| ZA (1) | ZA9610646B (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006054536A1 (ja) * | 2004-11-16 | 2006-05-26 | Nippon Shinyaku Co., Ltd. | 尿路結石症治療剤 |
| JP2008017734A (ja) * | 2006-07-11 | 2008-01-31 | Memory Secret Inc | 精神的機能を改善するための栄養補助及び栄養摂取食品用の口経投与組成物 |
| CN102485723A (zh) * | 2010-12-02 | 2012-06-06 | 江苏斯威森生物医药工程研究中心有限公司 | 一锅法半合成长春西汀及其水溶性盐制备 |
| CN114920743B (zh) * | 2022-05-09 | 2023-08-04 | 南京中医药大学 | 一种吲哚生物碱及其制备方法与应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2531108A1 (de) * | 1975-07-11 | 1977-02-03 | Synthelabo | Vincaminderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| HU186891B (en) * | 1981-06-12 | 1985-10-28 | Richter Gedeon Vegyeszet | Process for producing esters of apovincaminic acid |
| IT1142026B (it) * | 1981-07-21 | 1986-10-08 | Ausonia Farma Srl | Nuovo composto ad attivita' eumetabolica cerebrale |
| HU187733B (en) * | 1982-06-30 | 1986-02-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing apovincaminic acid derivatives |
| JPS60248688A (ja) * | 1984-05-24 | 1985-12-09 | Sanwa Kagaku Kenkyusho:Kk | 新規のアポビンカミン酸エステルおよびその酸付加塩並びにその製造方法 |
-
1995
- 1995-12-22 HU HU9503736A patent/HU214600B/hu not_active IP Right Cessation
-
1996
- 1996-12-13 AT AT96942534T patent/ATE223914T1/de not_active IP Right Cessation
- 1996-12-13 US US09/091,260 patent/US6093720A/en not_active Expired - Fee Related
- 1996-12-13 PT PT96942534T patent/PT876367E/pt unknown
- 1996-12-13 RU RU98113854/04A patent/RU2161157C2/ru not_active IP Right Cessation
- 1996-12-13 ES ES96942534T patent/ES2181926T3/es not_active Expired - Lifetime
- 1996-12-13 WO PCT/HU1996/000075 patent/WO1997023481A1/en active IP Right Grant
- 1996-12-13 CN CN96199131A patent/CN1072670C/zh not_active Expired - Fee Related
- 1996-12-13 CA CA002238635A patent/CA2238635A1/en not_active Abandoned
- 1996-12-13 CZ CZ19981962A patent/CZ290383B6/cs not_active IP Right Cessation
- 1996-12-13 IL IL12409796A patent/IL124097A/en not_active IP Right Cessation
- 1996-12-13 EP EP96942534A patent/EP0876367B1/en not_active Expired - Lifetime
- 1996-12-13 JP JP09523441A patent/JP2000502676A/ja not_active Withdrawn
- 1996-12-13 UA UA98052781A patent/UA61062C2/uk unknown
- 1996-12-13 PL PL96328170A patent/PL186626B1/pl not_active IP Right Cessation
- 1996-12-13 DK DK96942534T patent/DK0876367T3/da active
- 1996-12-13 DE DE69623656T patent/DE69623656T2/de not_active Expired - Fee Related
- 1996-12-13 KR KR1019980704700A patent/KR19990076606A/ko active IP Right Grant
- 1996-12-13 AU AU11669/97A patent/AU1166997A/en not_active Abandoned
- 1996-12-16 TW TW085115515A patent/TW366348B/zh active
- 1996-12-18 ZA ZA9610646A patent/ZA9610646B/xx unknown
- 1996-12-20 AR ARP960105829A patent/AR005182A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ196298A3 (cs) | 1998-10-14 |
| JP2000502676A (ja) | 2000-03-07 |
| EP0876367B1 (en) | 2002-09-11 |
| ES2181926T3 (es) | 2003-03-01 |
| CA2238635A1 (en) | 1997-07-03 |
| HU9503736D0 (en) | 1996-02-28 |
| WO1997023481A1 (en) | 1997-07-03 |
| US6093720A (en) | 2000-07-25 |
| ATE223914T1 (de) | 2002-09-15 |
| IL124097A (en) | 2001-12-23 |
| DE69623656T2 (de) | 2003-05-22 |
| DK0876367T3 (da) | 2002-12-30 |
| CN1205701A (zh) | 1999-01-20 |
| CN1072670C (zh) | 2001-10-10 |
| HUT76555A (en) | 1997-09-29 |
| TW366348B (en) | 1999-08-11 |
| PT876367E (pt) | 2003-01-31 |
| AR005182A1 (es) | 1999-04-14 |
| PL186626B1 (pl) | 2004-02-27 |
| CZ290383B6 (cs) | 2002-07-17 |
| HU214600B (hu) | 1998-04-28 |
| PL328170A1 (en) | 1999-01-18 |
| RU2161157C2 (ru) | 2000-12-27 |
| DE69623656D1 (en) | 2002-10-17 |
| EP0876367A1 (en) | 1998-11-11 |
| AU1166997A (en) | 1997-07-17 |
| KR19990076606A (ko) | 1999-10-15 |
| ZA9610646B (en) | 1997-06-24 |
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