DE2760316C2 - - Google Patents
Info
- Publication number
- DE2760316C2 DE2760316C2 DE2760316A DE2760316A DE2760316C2 DE 2760316 C2 DE2760316 C2 DE 2760316C2 DE 2760316 A DE2760316 A DE 2760316A DE 2760316 A DE2760316 A DE 2760316A DE 2760316 C2 DE2760316 C2 DE 2760316C2
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- benzo
- pyran
- dihydro
- formula
- Prior art date
- 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 - Lifetime
Links
- 239000000543 intermediate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000004880 oxines Chemical class 0.000 claims description 2
- AXWDPRJZZIUQPF-UHFFFAOYSA-N 2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene Chemical class CC1(C)OC2=CC=CC=C2C2C1O2 AXWDPRJZZIUQPF-UHFFFAOYSA-N 0.000 claims 1
- LKXADRQJLNYNQL-UHFFFAOYSA-N 2h-chromen-3-ol Chemical class C1=CC=C2OCC(O)=CC2=C1 LKXADRQJLNYNQL-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- -1 alkyl radical Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000014510 cooky Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical class BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 150000008371 chromenes Chemical class 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000012071 phase 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
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 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 description 1
- LSPMNHVVDOUFHQ-RCPFAERMSA-N (3s,4r)-3-hydroxy-2,2-dimethyl-4-piperidin-1-yl-3,4-dihydrochromene-6-carbonitrile;hydrochloride Chemical compound Cl.N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCCC1 LSPMNHVVDOUFHQ-RCPFAERMSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HHPHMEFAEUXBAX-UHFFFAOYSA-N 1-(2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromen-6-yl)ethanone Chemical compound O1C(C)(C)C2OC2C2=CC(C(=O)C)=CC=C21 HHPHMEFAEUXBAX-UHFFFAOYSA-N 0.000 description 1
- XUOKKNSMURHWLM-PPPUBMIESA-N 1-[(3s,4r)-3-hydroxy-2,2-dimethyl-4-piperidin-1-yl-3,4-dihydrochromen-6-yl]ethanone;hydrochloride Chemical compound Cl.N1([C@H]2[C@H](O)C(C)(C)OC3=CC=C(C=C32)C(=O)C)CCCCC1 XUOKKNSMURHWLM-PPPUBMIESA-N 0.000 description 1
- ALEQKJOHODTDTC-UHFFFAOYSA-N 2,3-dimethyl-2h-chromene Chemical compound C1=CC=C2C=C(C)C(C)OC2=C1 ALEQKJOHODTDTC-UHFFFAOYSA-N 0.000 description 1
- JIDPHLLCKDISON-UHFFFAOYSA-N 2h-pyran-4-ol Chemical compound OC1=CCOC=C1 JIDPHLLCKDISON-UHFFFAOYSA-N 0.000 description 1
- GMRZZEJZBSPVFQ-UHFFFAOYSA-N 3-bromo-2,2-dimethyl-3,4-dihydrochromen-4-ol Chemical compound C1=CC=C2C(O)C(Br)C(C)(C)OC2=C1 GMRZZEJZBSPVFQ-UHFFFAOYSA-N 0.000 description 1
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAJTXVHECZCXLH-UHFFFAOYSA-N desmethoxyencecalin Natural products O1C(C)(C)C=CC2=CC(C(=O)C)=CC=C21 ZAJTXVHECZCXLH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- APMKKPHGMDRZAF-WDEREUQCSA-N methyl (1ar,7bs)-2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene-6-carboxylate Chemical compound O1C(C)(C)[C@@H]2O[C@H]2C2=CC(C(=O)OC)=CC=C21 APMKKPHGMDRZAF-WDEREUQCSA-N 0.000 description 1
- TVBZFAJRSSQJLS-CVEARBPZSA-N methyl (3S,4R)-2,2-dimethyl-3-methylsulfonyloxy-4-pyrrolidin-1-yl-3,4-dihydrochromene-6-carboxylate Chemical compound CS(=O)(=O)O[C@H]1[C@@H](C2=C(OC1(C)C)C=CC(=C2)C(=O)OC)N2CCCC2 TVBZFAJRSSQJLS-CVEARBPZSA-N 0.000 description 1
- BVQOOKUOYKXECX-UHFFFAOYSA-N methyl 2,2-dimethylchromene-6-carboxylate Chemical compound O1C(C)(C)C=CC2=CC(C(=O)OC)=CC=C21 BVQOOKUOYKXECX-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- 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
-
- 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
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13536/76A GB1511187A (en) | 1976-04-02 | 1976-04-02 | Chromans |
| GB3317876 | 1976-08-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2760316C2 true DE2760316C2 (en, 2012) | 1993-12-23 |
| DE2760316C3 DE2760316C3 (de) | 1993-12-23 |
Family
ID=26249838
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772713670 Withdrawn DE2713670A1 (de) | 1976-04-02 | 1977-03-28 | Aminochromanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
| DE2760316A Expired - Lifetime DE2760316C3 (de) | 1976-04-02 | 1977-03-28 | Derivate des 3,4-Epoxy-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyrans und ihre Verwendung zur Herstellung von 2H-Benzo[b]pyran-3-olen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772713670 Withdrawn DE2713670A1 (de) | 1976-04-02 | 1977-03-28 | Aminochromanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4251537A (en, 2012) |
| JP (1) | JPS52122372A (en, 2012) |
| AU (1) | AU503934B2 (en, 2012) |
| CA (1) | CA1119180A (en, 2012) |
| CH (1) | CH632262A5 (en, 2012) |
| DE (2) | DE2713670A1 (en, 2012) |
| DK (1) | DK147777A (en, 2012) |
| ES (1) | ES457417A1 (en, 2012) |
| FR (1) | FR2346346A1 (en, 2012) |
| IE (1) | IE44977B1 (en, 2012) |
| IL (1) | IL51648A (en, 2012) |
| NL (2) | NL7703440A (en, 2012) |
| NZ (1) | NZ183551A (en, 2012) |
| SE (1) | SE7703715L (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0028064B1 (en) | 1979-09-28 | 1983-07-20 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and a pharmaceutical composition comprising them |
| DE3064285D1 (en) | 1979-09-28 | 1983-08-25 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and a pharmaceutical composition comprising them |
| EP0046652B1 (en) * | 1980-08-21 | 1985-05-22 | Beecham Group Plc | Chromanol derivatives, their production and pharmaceutical compositions containing them |
| US4447622A (en) * | 1981-09-22 | 1984-05-08 | Council Of Scientific And Industrial Research Rafi Marg | Preparation of l- and d-isomers of dl-3,4-trans-2,2-disubstituted-3,4-diarylchromans and derivatives thereof |
| DE3274350D1 (en) * | 1981-09-25 | 1987-01-08 | Beecham Group Plc | Pharmaceutically active benzopyran compounds |
| ZM7682A1 (en) * | 1981-09-25 | 1983-05-23 | Beecham Group Plc | Active compounds |
| US4404207A (en) * | 1981-11-06 | 1983-09-13 | Riker Laboratories, Inc. | Antimicrobial 8-substituted benzo [IJ]quinolizines |
| DE3364145D1 (de) * | 1982-04-08 | 1986-07-24 | Beecham Group Plc | Antihypertensive benzopyranols |
| DE3368057D1 (en) * | 1982-05-21 | 1987-01-15 | Beecham Group Plc | Pharmaceutically active aminobenzopyrans |
| GB8308063D0 (en) * | 1983-03-24 | 1983-05-05 | Beecham Group Plc | Active compounds |
| EP0139992B1 (en) * | 1983-09-01 | 1988-12-28 | Beecham Group Plc | Chromanol derivatives |
| PT84806B (pt) * | 1986-05-03 | 1989-12-29 | Beecham Group Plc | Processo para a preparacao de benzopiranos |
| DE3703227A1 (de) * | 1987-02-04 | 1988-08-18 | Hoechst Ag | Substituierte 3,4-dihydro-2h-benzopyrane, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| IL88035A0 (en) * | 1987-10-27 | 1989-06-30 | American Home Prod | Benzopyran derivatives,their preparation and pharmaceutical compositions containing them |
| DE3823533A1 (de) * | 1988-07-12 | 1990-02-08 | Beiersdorf Ag | Substituierte 4-heterocyclyl-2h-benzo(b)pyrane, verfahren und 4-hydroxy-3-brom-, 3,4-oxiranyl-3,4-dehydro-2h-benzo(b)pyrane als zwischenprodukte zu ihrer herstellung, sowie sie enthaltende pharmazeutsche praeparate |
| DE3827532A1 (de) * | 1988-08-13 | 1990-03-01 | Hoechst Ag | 6-aroyl-substituierte 3,4-dihydro-2h-benzopyrane, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| US4997846A (en) * | 1988-12-09 | 1991-03-05 | Researche Syntex France, S.A. | Novel benzopyranylpyrrolinone derivatives |
| US4908378A (en) * | 1989-04-12 | 1990-03-13 | American Home Products Corporation | Benzopyran derivatives and antihypertensive use thereof |
| DE3923839A1 (de) * | 1989-07-19 | 1991-01-31 | Beiersdorf Ag | Benzopyran-derivate, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen |
| US5837702A (en) * | 1993-10-07 | 1998-11-17 | Bristol-Myers Squibb Co. | 4-arylamino-benzopyran and related compounds |
| US5612323A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phosphinic ester substituted benzopyran derivatives |
| 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 |
| US5612370A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phenylglycine and phenylalaninen amido benzopyran derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2523281A1 (de) * | 1974-05-31 | 1975-12-11 | Beecham Group Ltd | Derivate des trans-3-hydroxy-4-amino-chromans, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0076075B1 (en) * | 1981-09-25 | 1986-11-20 | Beecham Group Plc | Pharmaceutically active benzopyran compounds |
-
1977
- 1977-03-09 NZ NZ183551A patent/NZ183551A/xx unknown
- 1977-03-11 IL IL51648A patent/IL51648A/xx unknown
- 1977-03-28 FR FR7709151A patent/FR2346346A1/fr active Granted
- 1977-03-28 DE DE19772713670 patent/DE2713670A1/de not_active Withdrawn
- 1977-03-28 DE DE2760316A patent/DE2760316C3/de not_active Expired - Lifetime
- 1977-03-29 CH CH394477A patent/CH632262A5/de not_active IP Right Cessation
- 1977-03-30 SE SE7703715A patent/SE7703715L/xx unknown
- 1977-03-30 JP JP3603477A patent/JPS52122372A/ja active Granted
- 1977-03-30 NL NL7703440A patent/NL7703440A/xx active Search and Examination
- 1977-03-31 ES ES457417A patent/ES457417A1/es not_active Expired
- 1977-04-01 IE IE694/77A patent/IE44977B1/en unknown
- 1977-04-01 CA CA000275337A patent/CA1119180A/en not_active Expired
- 1977-04-01 AU AU23875/77A patent/AU503934B2/en not_active Expired
- 1977-04-01 DK DK147777A patent/DK147777A/da not_active IP Right Cessation
-
1978
- 1978-12-18 US US05/970,199 patent/US4251537A/en not_active Expired - Lifetime
-
1984
- 1984-09-06 NL NL8402722A patent/NL8402722A/nl active Search and Examination
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2523281A1 (de) * | 1974-05-31 | 1975-12-11 | Beecham Group Ltd | Derivate des trans-3-hydroxy-4-amino-chromans, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0076075B1 (en) * | 1981-09-25 | 1986-11-20 | Beecham Group Plc | Pharmaceutically active benzopyran compounds |
Non-Patent Citations (1)
| Title |
|---|
| GB-Z.: J.Chem. Soc., London, (1962), S. 76-79 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DK147777A (da) | 1977-10-03 |
| IL51648A (en) | 1982-08-31 |
| FR2346346A1 (fr) | 1977-10-28 |
| AU503934B2 (en) | 1979-09-27 |
| SE7703715L (sv) | 1977-10-03 |
| JPS52122372A (en) | 1977-10-14 |
| NZ183551A (en) | 1978-09-20 |
| DE2713670A1 (de) | 1977-10-06 |
| US4251537A (en) | 1981-02-17 |
| IE44977L (en) | 1977-10-02 |
| FR2346346B1 (en, 2012) | 1980-03-07 |
| DE2760316C3 (de) | 1993-12-23 |
| NL8402722A (nl) | 1984-12-03 |
| ES457417A1 (es) | 1978-07-16 |
| CA1119180A (en) | 1982-03-02 |
| CH632262A5 (de) | 1982-09-30 |
| IE44977B1 (en) | 1982-06-02 |
| NL7703440A (nl) | 1977-10-04 |
| AU2387577A (en) | 1978-10-12 |
| IL51648A0 (en) | 1977-05-31 |
| JPS6112910B2 (en, 2012) | 1986-04-10 |
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