NO802345L - Fremgangsmaate ved fremstilling av nye, halogenerte 15-hydroxy-e-homoeburnanderivater - Google Patents

Fremgangsmaate ved fremstilling av nye, halogenerte 15-hydroxy-e-homoeburnanderivater

Info

Publication number: NO802345L
Authority: NO; Norway
Prior art keywords: acid; hydroxy; general formula; homoeburnane; compounds
Prior art date: 1979-08-06

Application number

NO802345A

Other languages

English (en)

Norwegian (no)

Inventor

Csaba Szantay

Lajos Szabo

Gyoergy Kalaus

Lajos Dancsi

Tibor Keve

Ferenc Draxler

Original Assignee

Richter Gedeon Vegyeszet

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.)

1979-08-06

Filing date

1980-08-05

Publication date

1981-02-09

1980-08-05 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1981-02-09 Publication of NO802345L publication Critical patent/NO802345L/no

Links

238000000034 method Methods 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims description 22
239000002253 acid Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 4
239000002841 Lewis acid Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
230000026030 halogenation Effects 0.000 claims 1
238000005658 halogenation reaction Methods 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
239000002904 solvent Substances 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
-1 bromine compound Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
239000000155 melt Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
229940044631 ferric chloride hexahydrate Drugs 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000012746 preparative thin layer chromatography Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000011877 solvent mixture Substances 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229960004889 salicylic acid Drugs 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
238000000926 separation method Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 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
HBBBDGWCSBWWKP-UHFFFAOYSA-J tetrachloroantimony Chemical compound Cl[Sb](Cl)(Cl)Cl HBBBDGWCSBWWKP-UHFFFAOYSA-J 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
- 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
- A61P9/08—Vasodilators for multiple indications

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO802345A 1979-08-06 1980-08-05 Fremgangsmaate ved fremstilling av nye, halogenerte 15-hydroxy-e-homoeburnanderivater NO802345L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU79RI721A HU180928B (en)	1979-08-06	1979-08-06	Process for preparing new brominated 15-hydroxy-e-homo-eburane derivatives

Publications (1)

Publication Number	Publication Date
NO802345L true NO802345L (no)	1981-02-09

Family

ID=11001104

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO802345A NO802345L (no)	1979-08-06	1980-08-05	Fremgangsmaate ved fremstilling av nye, halogenerte 15-hydroxy-e-homoeburnanderivater

Country Status (22)

Country	Link
US (2)	US4285865A (es)
JP (1)	JPS5636488A (es)
AT (1)	AT375080B (es)
AU (1)	AU534494B2 (es)
BE (1)	BE884567A (es)
CA (1)	CA1137473A (es)
CH (1)	CH647779A5 (es)
DE (1)	DE3026601A1 (es)
DK (1)	DK337180A (es)
ES (1)	ES494034A0 (es)
FI (1)	FI70021C (es)
GB (1)	GB2058756B (es)
HU (1)	HU180928B (es)
IL (1)	IL60587A (es)
IT (1)	IT1132533B (es)
NL (1)	NL8004350A (es)
NO (1)	NO802345L (es)
NZ (1)	NZ194571A (es)
PH (1)	PH15612A (es)
SE (1)	SE438858B (es)
SU (1)	SU931107A3 (es)
ZA (1)	ZA804302B (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU180927B (en) *	1979-07-13	1983-05-30	Richter Gedeon Vegyeszet	Process for producing 1k-hydroximino-e-homoe-eburane de rivatives
HU180929B (en) *	1979-08-13	1983-05-30	Richter Gedeon Vegyeszet	Process for producing new bromo-vincamone derivatives
HU187139B (en) *	1982-06-30	1985-11-28	Richter Gedeon Vegyeszet	Process for preparing new eburnan derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3770724A (en) *	1970-03-31	1973-11-06	Roussel Uclaf	Process for preparing pentacyclic alkaloids
FR2206090A1 (en) *	1972-11-16	1974-06-07	Omnium Chimique Sa	Homovincamone-contg. medicaments - with vasodilating, spasmolytic anti-arrhythmic and anti-ischaemic properties
DK139358B (da) *	1973-12-18	1979-02-05	Sandoz Ag	Analogifremgangsmåde til fremstilling af vincaminderivater eller syreadditionssalte deraf.
GB2010833B (en) *	1977-11-25	1982-04-15	Scras	Homoerburnamine preparation
FR2445328A1 (fr) *	1978-07-12	1980-07-25	Richter Gedeon Vegyeszet	Derives du 14-oxo-e-homo-eburnane, leur procede de preparation et leur utilisation comme medicament

1979
- 1979-08-06 HU HU79RI721A patent/HU180928B/hu not_active IP Right Cessation
1980
- 1980-07-14 DE DE19803026601 patent/DE3026601A1/de not_active Withdrawn
- 1980-07-15 IL IL60587A patent/IL60587A/xx unknown
- 1980-07-16 ZA ZA00804302A patent/ZA804302B/xx unknown
- 1980-07-24 PH PH24345A patent/PH15612A/en unknown
- 1980-07-30 NL NL8004350A patent/NL8004350A/xx not_active Application Discontinuation
- 1980-07-31 BE BE1/9913A patent/BE884567A/fr not_active IP Right Cessation
- 1980-07-31 AT AT0396480A patent/AT375080B/de not_active IP Right Cessation
- 1980-08-01 FI FI802410A patent/FI70021C/fi not_active IP Right Cessation
- 1980-08-05 DK DK337180A patent/DK337180A/da not_active Application Discontinuation
- 1980-08-05 SE SE8005560A patent/SE438858B/sv not_active IP Right Cessation
- 1980-08-05 US US06/175,385 patent/US4285865A/en not_active Expired - Lifetime
- 1980-08-05 NO NO802345A patent/NO802345L/no unknown
- 1980-08-05 JP JP10684780A patent/JPS5636488A/ja active Pending
- 1980-08-05 IT IT24015/80A patent/IT1132533B/it active
- 1980-08-05 SU SU802954159A patent/SU931107A3/ru active
- 1980-08-05 NZ NZ194571A patent/NZ194571A/xx unknown
- 1980-08-05 AU AU61103/80A patent/AU534494B2/en not_active Ceased
- 1980-08-05 CH CH5922/80A patent/CH647779A5/de not_active IP Right Cessation
- 1980-08-06 GB GB8025577A patent/GB2058756B/en not_active Expired
- 1980-08-06 CA CA000357709A patent/CA1137473A/en not_active Expired
- 1980-08-06 ES ES494034A patent/ES494034A0/es active Granted
- 1980-12-16 US US06/216,903 patent/US4343738A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DK337180A (da)	1981-02-07
GB2058756B (en)	1984-02-08
ES8106526A1 (es)	1981-08-01
JPS5636488A (en)	1981-04-09
IT1132533B (it)	1986-07-02
GB2058756A (en)	1981-04-15
SE438858B (sv)	1985-05-13
AT375080B (de)	1984-06-25
IL60587A (en)	1983-05-15
AU534494B2 (en)	1984-02-02
FI802410A (fi)	1981-02-07
PH15612A (en)	1983-02-28
CH647779A5 (de)	1985-02-15
IL60587A0 (en)	1980-09-16
CA1137473A (en)	1982-12-14
ZA804302B (en)	1981-09-30
AU6110380A (en)	1981-02-12
DE3026601A1 (de)	1981-02-26
IT8024015A0 (it)	1980-08-05
FI70021B (fi)	1986-01-31
HU180928B (en)	1983-05-30
SE8005560L (sv)	1981-02-07
BE884567A (fr)	1981-02-02
ATA396480A (de)	1983-11-15
SU931107A3 (ru)	1982-05-23
ES494034A0 (es)	1981-08-01
US4285865A (en)	1981-08-25
NZ194571A (en)	1982-11-23
NL8004350A (nl)	1981-02-10
US4343738A (en)	1982-08-10
FI70021C (fi)	1986-09-12

Publication	Publication Date	Title
CN112174989B (zh)	2023-06-20	一种克立硼罗的制备方法
US4283401A (en)	1981-08-11	Process for the preparation of 11-bromo-vincaminic acid ester derivatives and their use in protecting animals against cerebral hypoxy
SU612631A3 (ru)	1978-06-25	Способ получени -(тетрагидрофурфурил)нороксиморфонов или их солей
NO802345L (no)	1981-02-09	Fremgangsmaate ved fremstilling av nye, halogenerte 15-hydroxy-e-homoeburnanderivater
US3978085A (en)	1976-08-31	Process for benz[f]-2,5-oxazocines
US4314939A (en)	1982-02-09	Process for the preparation of 15-hydroxyimino-E-homoeburnane and intermediates therefor
JPS5910674B2 (ja)	1984-03-10	アポビンカミン酸エステルの製法
Pelletier et al.	1982	The pyrodelphonine chromophore. Crystal structures of pyrodelphinine and delphinine
JPS6317077B2 (es)	1988-04-12
JPH01313474A (ja)	1989-12-18	５‐クロル‐３‐クロルスルホニル‐２‐チオフエンカルボン酸エステルの製造方法
SU1711674A3 (ru)	1992-02-07	Способ получени азонийспиронортропанолового сложного эфира
US5552533A (en)	1996-09-03	Preparation of (8S)-8-fluoroerythromycins with N-F fluorinating agents
Oda et al.	1983	Microbial transformation of (+)-and (-)-2'-demethoxydehydrogriseofulvin by Streptomyces cinereocrocatus
Kumar et al.	1986	Synthesis of dihydrodiols and diol epoxides of dibenz [a, h] acridine
US5142091A (en)	1992-08-25	α, β-unsaturated ketones and ketoxime derivatives
EP0050492A1 (en)	1982-04-28	1,1-Disubstituted-hexahydro-indolo(2,3-a)quinolizine derivatives and their use in the enantioselective synthesis of optically active 14-oxo-E-homo-eburnane derivatives
NO822864L (no)	1983-02-24	Fremgangsmaate ved fremstilling av alkoxy-vincaminsyreestere og alkoxy-apovincaminsyreestere
US4649202A (en)	1987-03-10	Brominative aromatization of 4-cyclohexenylpyridines
US4758666A (en)	1988-07-19	Process for the preparation of an apovincaminol derivative
US4727148A (en)	1988-02-23	Certain aromatization process for preparing 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinoline carboxylic acid
DK149956B (da)	1986-11-03	Fremgangsmaade til fremstilling af bromholdige ergotalkaloider
JPS6111952B2 (es)	1986-04-05
GB2061940A (en)	1981-05-20	Process for the preparation of 11-bromo-E-homoeburnane derivatives
JPH07316136A (ja)	1995-12-05	ベンゾキノリノンの合成
JP2001199985A (ja)	2001-07-24	高純度フェノチアジン化合物とその製造方法、およびその中間体の製造方法、並びにその中間体の原料の水和物と新規結晶