SK362990A3 - Method for producing (+/-)-6-cyano-3, 4-dihydro-2,2-dimethyl- -trans-4-(2-oxo-1-pyrrolidinyl)-2h-1-benzopyran-3-ol - Google Patents

Method for producing (+/-)-6-cyano-3, 4-dihydro-2,2-dimethyl- -trans-4-(2-oxo-1-pyrrolidinyl)-2h-1-benzopyran-3-ol Download PDF

Info

Publication number: SK362990A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; hours; cyano; temperature
Prior art date: 1989-07-21

Application number

SK3629-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK278873B6 (sk

Inventor

Tibor Timar

Tibor Eszenyi

Peter Sebok

Vilmos Galamb

Julia Fazekas

Terezia Istvan

Eva Kovach

Erika Nagy

Original Assignee

Alkaloida Vegyeszeti Gyar

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.)

1989-07-21

Filing date

1990-07-20

Publication date

1998-04-08

1990-07-20 Application filed by Alkaloida Vegyeszeti Gyar filed Critical Alkaloida Vegyeszeti Gyar

1998-04-08 Publication of SK278873B6 publication Critical patent/SK278873B6/sk

1998-04-08 Publication of SK362990A3 publication Critical patent/SK362990A3/sk

Links

238000004519 manufacturing process Methods 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 61
238000000034 method Methods 0.000 claims abstract description 43
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract description 33
239000002904 solvent Substances 0.000 claims abstract description 28
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 claims abstract description 23
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 22
238000002360 preparation method Methods 0.000 claims abstract description 19
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract description 16
150000001340 alkali metals Chemical class 0.000 claims abstract description 15
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 9
NBUWNTIATBQVDR-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound N#CC1=CC=C2OC(C)(C)CCC2=C1 NBUWNTIATBQVDR-UHFFFAOYSA-N 0.000 claims abstract description 8
239000003054 catalyst Substances 0.000 claims abstract description 7
YDEQIYMIVRCVAH-UHFFFAOYSA-N 2,2-dimethylchromene-6-carbonitrile Chemical compound C1=C(C#N)C=C2C=CC(C)(C)OC2=C1 YDEQIYMIVRCVAH-UHFFFAOYSA-N 0.000 claims abstract description 6
230000031709 bromination Effects 0.000 claims abstract description 5
238000005893 bromination reaction Methods 0.000 claims abstract description 5
150000004965 peroxy acids Chemical class 0.000 claims abstract description 5
HCYIWPLDKSWKGY-UHFFFAOYSA-N 2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene-6-carbonitrile Chemical compound CC1(C)OC2=CC=C(C#N)C=C2C2C1O2 HCYIWPLDKSWKGY-UHFFFAOYSA-N 0.000 claims abstract description 4
238000007269 dehydrobromination reaction Methods 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
239000012467 final product Substances 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
229910001868 water Inorganic materials 0.000 claims description 13
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 12
-1 alkali metal alkoxide Chemical class 0.000 claims description 10
TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
239000003849 aromatic solvent Substances 0.000 claims description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
229960000583 acetic acid Drugs 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
239000012362 glacial acetic acid Substances 0.000 claims description 3
229940046892 lead acetate Drugs 0.000 claims description 3
235000011007 phosphoric acid Nutrition 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
239000000047 product Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
239000002841 Lewis acid Substances 0.000 claims description 2
235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
150000007517 lewis acids Chemical class 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
238000006356 dehydrogenation reaction Methods 0.000 claims 3
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims 2
125000001743 benzylic group Chemical group 0.000 claims 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
238000007171 acid catalysis Methods 0.000 claims 1
239000003377 acid catalyst Substances 0.000 claims 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
150000004703 alkoxides Chemical class 0.000 claims 1
239000007864 aqueous solution Substances 0.000 claims 1
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
150000008282 halocarbons Chemical class 0.000 claims 1
230000003647 oxidation Effects 0.000 claims 1
238000007254 oxidation reaction Methods 0.000 claims 1
239000001103 potassium chloride Substances 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 abstract description 4
PKZZJLKUYUVLMJ-MNOVXSKESA-N (3s,4r)-3-bromo-4-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C1=C(C#N)C=C2[C@@H](O)[C@H](Br)C(C)(C)OC2=C1 PKZZJLKUYUVLMJ-MNOVXSKESA-N 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract 1
239000011541 reaction mixture Substances 0.000 description 15
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
150000002924 oxiranes Chemical class 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
229950004210 cromakalim Drugs 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
229960001760 dimethyl sulfoxide Drugs 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000012230 colorless oil Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
MMSFHQSHXRMPLJ-CVEARBPZSA-N (3s,4r)-3-hydroxy-2,2-dimethyl-4-(2-oxopyridin-1-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)C=CC=CC1=O MMSFHQSHXRMPLJ-CVEARBPZSA-N 0.000 description 1
APHWBGUCQBONMO-MNOVXSKESA-N (3s,4r)-4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C1=C(C#N)C=C2[C@@H](N)[C@H](O)C(C)(C)OC2=C1 APHWBGUCQBONMO-MNOVXSKESA-N 0.000 description 1
SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
MITIYLBEZOKYLX-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromene Chemical class C1=CC=C2OC(C)(C)CCC2=C1 MITIYLBEZOKYLX-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
ASPPGMMWYKVWNH-UHFFFAOYSA-N 3-benzyl-1-bromopyrrolidine-2,5-dione Chemical compound C(C1=CC=CC=C1)C1C(=O)N(C(C1)=O)Br ASPPGMMWYKVWNH-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
102000004257 Potassium Channel Human genes 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
SOUGLODYPBMACB-UHFFFAOYSA-N butane;hydrate Chemical compound O.CCCC SOUGLODYPBMACB-UHFFFAOYSA-N 0.000 description 1
150000008371 chromenes Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 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
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000009434 installation Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
108020001213 potassium channel Proteins 0.000 description 1
239000004036 potassium channel stimulating agent Substances 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4

Landscapes

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

SK3629-90A 1989-07-21 1990-07-20 Method for producing (+/-)-6-cyano-3, 4-dihydro-2,2-dimethyl- -trans-4-(2-oxo-1-pyrrolidinyl)-2h-1-benzopyran-3-ol SK362990A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU893699A HU207861B (en)	1989-07-21	1989-07-21	Process for producing benzopirane derivative of blood pressure lowering activity

Publications (2)

Publication Number	Publication Date
SK278873B6 SK278873B6 (sk)	1998-04-08
SK362990A3 true SK362990A3 (en)	1998-04-08

Family

ID=10965123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK3629-90A SK362990A3 (en)	1989-07-21	1990-07-20	Method for producing (+/-)-6-cyano-3, 4-dihydro-2,2-dimethyl- -trans-4-(2-oxo-1-pyrrolidinyl)-2h-1-benzopyran-3-ol

Country Status (12)

Country	Link
US (1)	US5145985A (cs)
EP (1)	EP0409651B1 (cs)
JP (1)	JPH0358988A (cs)
CZ (1)	CZ283969B6 (cs)
DE (1)	DE69019080T2 (cs)
ES (1)	ES2072982T3 (cs)
HU (1)	HU207861B (cs)
IL (1)	IL95143A (cs)
PL (1)	PL286145A1 (cs)
RU (2)	RU2036196C1 (cs)
SK (1)	SK362990A3 (cs)
YU (1)	YU139090A (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5837702A (en) *	1993-10-07	1998-11-17	Bristol-Myers Squibb Co.	4-arylamino-benzopyran and related compounds
US5629429A (en) *	1995-06-07	1997-05-13	Bristol-Myers Squibb Company	Process for preparing 4-arylamino-benzopyran and related compounds
US5869478A (en) *	1995-06-07	1999-02-09	Bristol-Myers Squibb Company	Sulfonamido substituted benzopyran derivatives
US5612323A (en) *	1995-06-07	1997-03-18	Bristol-Myers Squibb Company	Phosphinic ester substituted benzopyran derivatives
US5612370A (en) *	1995-06-07	1997-03-18	Bristol-Myers Squibb Company	Phenylglycine and phenylalaninen amido benzopyran derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4391815A (en) *	1976-04-02	1983-07-05	Beecham Group Limited	Cyanobenzano[b]pyrans
DE2851207A1 (de) *	1977-12-06	1979-06-07	Garcia De Lama Javier	Verfahren zur herstellung substituierter 4h-pyran-4-one
ATE23718T1 (de) *	1981-09-25	1986-12-15	Beecham Group Plc	Benzopyran-verbindungen mit pharmazeutischer wirkung.
HU194214B (en) *	1983-02-15	1988-01-28	Alkaloida Vegyeszeti Gyar	Process for producing 7-alkoxy-2h-chromene derivatives and insecticide and nematocide compositions containing them as active components
GB8308062D0 (en) *	1983-03-24	1983-05-05	Beecham Group Plc	Active compounds

1989
- 1989-07-21 HU HU893699A patent/HU207861B/hu not_active IP Right Cessation
1990
- 1990-06-25 US US07/543,142 patent/US5145985A/en not_active Expired - Fee Related
- 1990-07-17 YU YU139090A patent/YU139090A/sh unknown
- 1990-07-20 JP JP2193788A patent/JPH0358988A/ja active Pending
- 1990-07-20 PL PL28614590A patent/PL286145A1/xx unknown
- 1990-07-20 SK SK3629-90A patent/SK362990A3/sk unknown
- 1990-07-20 IL IL9514390A patent/IL95143A/en not_active IP Right Cessation
- 1990-07-20 DE DE69019080T patent/DE69019080T2/de not_active Expired - Fee Related
- 1990-07-20 EP EP90307975A patent/EP0409651B1/en not_active Expired - Lifetime
- 1990-07-20 RU SU904830502A patent/RU2036196C1/ru active
- 1990-07-20 ES ES90307975T patent/ES2072982T3/es not_active Expired - Lifetime
- 1990-07-20 CZ CS903629A patent/CZ283969B6/cs unknown
1992
- 1992-02-19 RU SU925010854A patent/RU2041223C1/ru active

Also Published As

Publication number	Publication date
IL95143A (en)	1996-10-31
DE69019080D1 (de)	1995-06-08
JPH0358988A (ja)	1991-03-14
RU2041223C1 (ru)	1995-08-09
SK278873B6 (sk)	1998-04-08
YU139090A (sh)	1993-05-28
US5145985A (en)	1992-09-08
DE69019080T2 (de)	1995-11-02
ES2072982T3 (es)	1995-08-01
CZ362990A3 (cs)	1998-03-18
HUT58321A (en)	1992-02-28
IL95143A0 (en)	1991-06-10
CZ283969B6 (cs)	1998-07-15
RU2036196C1 (ru)	1995-05-27
HU207861B (en)	1993-06-28
PL286145A1 (en)	1991-07-15
EP0409651A1 (en)	1991-01-23
EP0409651B1 (en)	1995-05-03

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