JPS6148839B2 - - Google Patents

Info

Publication number: JPS6148839B2
Authority: JP; Japan
Prior art keywords: general formula; acid; optically active; vincamic; racemized
Prior art date: 1977-05-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP12015083A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5993079A (ja

Inventor

Zantai Saba

Zabo Rayosu

Karausu Joruji

Kuraidoru Yanosu

Fuarukasu Ienone

Nemesu Andorasu

Berusukai Hedoihi

Rakuzunaa Katarin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

RIHITAA GEDEON BEGIESUZECHI GIARU AARU TEII

Original Assignee

RIHITAA GEDEON BEGIESUZECHI GIARU AARU TEII

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-05-26

Filing date

1983-07-01

Publication date

1986-10-25

1983-07-01 Application filed by RIHITAA GEDEON BEGIESUZECHI GIARU AARU TEII filed Critical RIHITAA GEDEON BEGIESUZECHI GIARU AARU TEII

1984-05-29 Publication of JPS5993079A publication Critical patent/JPS5993079A/ja

1986-10-25 Publication of JPS6148839B2 publication Critical patent/JPS6148839B2/ja

Status Granted legal-status Critical Current

Links

239000002253 acid Substances 0.000 claims description 53
150000002148 esters Chemical class 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
230000006340 racemization Effects 0.000 claims 3
230000003287 optical effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 33
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
239000000203 mixture Substances 0.000 description 20
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 11
239000007858 starting material Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000000908 ammonium hydroxide Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
229960002726 vincamine Drugs 0.000 description 6
239000002585 base Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000012670 alkaline solution Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 3
229950006936 apovincamine Drugs 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
-1 etc. Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP12015083A 1977-05-26 1983-07-01 ビンカミン酸エステルの製法 Granted JPS5993079A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HURI000634 HU180514B (hu)	1977-05-26	1977-05-26	Eljárás apovinkaminsav-észterek, illetve vinkaminsav-észterek és apovinkaminsavészterek egyidejű előállítására
HU634		1977-05-26

Publications (2)

Publication Number	Publication Date
JPS5993079A JPS5993079A (ja)	1984-05-29
JPS6148839B2 true JPS6148839B2 (no)	1986-10-25

Family

ID=11001031

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
JP53061757A Expired JPS5910674B2 (ja)	1977-05-26	1978-05-25	アポビンカミン酸エステルの製法
JP12015083A Granted JPS5993079A (ja)	1977-05-26	1983-07-01	ビンカミン酸エステルの製法
JP12014983A Granted JPS5993078A (ja)	1977-05-26	1983-07-01	ヒドロキシアミノ−エブルナン誘導体およびその製法

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
JP53061757A Expired JPS5910674B2 (ja)	1977-05-26	1978-05-25	アポビンカミン酸エステルの製法

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP12014983A Granted JPS5993078A (ja)	1977-05-26	1983-07-01	ヒドロキシアミノ−エブルナン誘導体およびその製法

Country Status (2)

Country	Link
JP (3)	JPS5910674B2 (no)
HU (1)	HU180514B (no)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4446139A (en) *	1979-05-31	1984-05-01	Richter Gedeon Vegyeszeti Gyar R.T.	Hexahydroindoloquinolizinium and octahydroindoloquinolizine esters, and method of increasing blood flow in an animal with hydroxyamino-eburnane derivatives
HU181495B (en) *	1979-05-31	1983-07-28	Richter Gedeon Vegyeszet	Process for producing hydroxy-imino-eburnane derivatives
HU180927B (en) *	1979-07-13	1983-05-30	Richter Gedeon Vegyeszet	Process for producing 1k-hydroximino-e-homoe-eburane de rivatives
IL60613A (en) *	1979-08-16	1983-12-30	Richter Gedeon Vegyeszet	Dermatological compositions applicable directly to the skin comprising an eburnamenine derivative and process for their preparation
JPH0258618U (no) *	1988-10-25	1990-04-26
JP4961567B2 (ja) *	2008-07-29	2012-06-27	道子遠藤	スライド式コンセントテーブルタップ

1977
- 1977-05-26 HU HURI000634 patent/HU180514B/hu not_active IP Right Cessation
1978
- 1978-05-25 JP JP53061757A patent/JPS5910674B2/ja not_active Expired
1983
- 1983-07-01 JP JP12015083A patent/JPS5993079A/ja active Granted
- 1983-07-01 JP JP12014983A patent/JPS5993078A/ja active Granted

Also Published As

Publication number	Publication date
HU180514B (hu)	1983-03-28
JPS5993078A (ja)	1984-05-29
JPS5910674B2 (ja)	1984-03-10
JPS5993079A (ja)	1984-05-29
JPS616072B2 (no)	1986-02-24
JPS53147100A (en)	1978-12-21

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SU588916A3 (ru)	1978-01-15	Способ получени 2-тетрагидрофурил-6,7-бензоморфанов или их солей
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JPS6148839B2 (no)	1986-10-25
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Brine et al.	1990	An improved resolution of (±)‐cis‐N‐normetazocine
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US4704472A (en)	1987-11-03	Preparation of an enantiomer of a substituted fluorenyloxyacetic acid
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US5352790A (en)	1994-10-04	Process for the preparation of 1β-ethyl-1α-(hydroxymethyl)-1,2,3,4,6,7,12,12Bα-octahydro-indolo[2,3,-A]quinolizine and novel intermediates
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