ES469202A1 - Novel benzo *c* quinolines - Google Patents
Novel benzo *c* quinolinesInfo
- Publication number
- ES469202A1 ES469202A1 ES469202A ES469202A ES469202A1 ES 469202 A1 ES469202 A1 ES 469202A1 ES 469202 A ES469202 A ES 469202A ES 469202 A ES469202 A ES 469202A ES 469202 A1 ES469202 A1 ES 469202A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- carbon atoms
- hydrogen
- integer
- 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
Links
- 125000005605 benzo group Chemical group 0.000 title abstract 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 150000003248 quinolines Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- 229910052739 hydrogen Inorganic materials 0.000 abstract 10
- 239000001257 hydrogen Substances 0.000 abstract 10
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- -1 pyrrolo Chemical group 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A method for preparing a compound that can be used as an intermediate in obtaining new benzo [c] kineleins that have activity on the central nervous system, said intermediates having the formula: (See formula) where R1 is selected from the group consisting of hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms and -CO- (CH2) p-NR2P3 where p is 0 or an integer from 1 to 4; each of R2 and R3 when taken individually is selected from the group consisting of hydrogen or alkyl having from one to four carbon atoms; R2 and R3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring, selected from the group consisting of piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having one to four carbon atoms in the alkyl group; R4 is selected from the group consisting of hydrogen, alkyl having 1 to 6 carbon atoms, and - (CH2) z-C6H5 where z is an integer from 1 to 4; R5 is selected from the group consisting of hydrogen, methyl, and ethyl; R6 is selected from the group consisting of hydrogen, - (CH2) and -carbalkoxy having one to four carbon atoms in the alkoxy group and y is 0 or an integer from 1 to 4, carbobenzyloxy, formyl, alkanoyl having two to five carbon atoms, alkyl having from one to six carbon atoms; - (CH2) x-C6H5 where x is an integer from 1 to 4; and -CO (CH2) x-1-C6H5; R0 is selected from the group consisting of oxo, methylene, and alkylondioxy having two to four carbon atoms; R'is selected from the group consisting of R and R0; Z is selected from the group consisting of (a) alkylene having one to nine carbon atoms; (b) - (alk1) mX- (alk2) n- where each of (alk1) and (alk2) is alkylene having one to nine carbon atoms, with the proviso that the sum of carbon atoms in (alk1) plus (alk2) is not greater than nine; each of m and n is 0 or 1; X is selected from the group consisting of O, S, SO, and SO2; and W is selected from the group consisting of hydrogen, methyl, pyridyl, piperidyl, (see formula) wherein W1 is selected from the group consisting of hydrogen, fluorine, and chlorine; and (see formula) where W2 is selected from the group consisting of hydrogen and (see formula) a is an integer from 1 to 5 and b is 0 or an integer from 1 to 5; with the proviso that the sum of a and b is not greater than 5; and ketals of compounds of formula III wherein the ketal moiety has two to four carbon atoms, characterized by reacting a compound of formula (See formula) where R1 is hydrogen, benzyl, methyl or ethyl; R4, R5, Z and W are as defined above; and R7 is hydrogen or fornyl, with a base, and if desired, ketalizing or thioketalizing a compound of formula III. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68733276A | 1976-05-17 | 1976-05-17 | |
| US75361976A | 1976-12-22 | 1976-12-22 | |
| US77792877A | 1977-03-15 | 1977-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES469202A1 true ES469202A1 (en) | 1978-11-16 |
Family
ID=27418484
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES458812A Expired ES458812A1 (en) | 1976-05-17 | 1977-05-14 | Novel benzo *c* quinolines |
| ES469203A Expired ES469203A1 (en) | 1976-05-17 | 1978-04-27 | Novel benzo *c* quinolines |
| ES469202A Expired ES469202A1 (en) | 1976-05-17 | 1978-04-27 | Novel benzo *c* quinolines |
| ES469204A Expired ES469204A1 (en) | 1976-05-17 | 1978-04-27 | Novel benzo *c* quinolines |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES458812A Expired ES458812A1 (en) | 1976-05-17 | 1977-05-14 | Novel benzo *c* quinolines |
| ES469203A Expired ES469203A1 (en) | 1976-05-17 | 1978-04-27 | Novel benzo *c* quinolines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES469204A Expired ES469204A1 (en) | 1976-05-17 | 1978-04-27 | Novel benzo *c* quinolines |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS6016426B2 (en) |
| AR (1) | AR215896A1 (en) |
| BG (4) | BG28415A4 (en) |
| CA (1) | CA1095909A (en) |
| CH (2) | CH626881A5 (en) |
| DD (1) | DD130855A5 (en) |
| DE (1) | DE2722383A1 (en) |
| DK (1) | DK212677A (en) |
| ES (4) | ES458812A1 (en) |
| FI (1) | FI64141C (en) |
| FR (2) | FR2362129A1 (en) |
| GR (1) | GR74122B (en) |
| IL (1) | IL52087A (en) |
| LU (1) | LU77341A1 (en) |
| NL (2) | NL170141C (en) |
| NO (1) | NO147028C (en) |
| NZ (1) | NZ184114A (en) |
| PH (1) | PH16833A (en) |
| PT (1) | PT66550B (en) |
| RO (1) | RO76839A (en) |
| SE (1) | SE7704749L (en) |
| SU (1) | SU1098520A3 (en) |
| YU (2) | YU156882A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2802211A1 (en) * | 1978-01-19 | 1979-07-26 | Basf Ag | N-SUBSTITUTED 2,6-DIALKYLANILINES AND METHOD FOR PREPARING N-SUBSTITUTED 2,6-DIALKYLANILINES |
| US4206225A (en) * | 1978-09-22 | 1980-06-03 | Pfizer Inc. | 2,10-Disubstituted dibenzo[b,d]pyrans and benzo[c]quinolines |
| US4228169A (en) * | 1979-06-26 | 1980-10-14 | Pfizer Inc. | 1,9-Dihydroxyoctahydrobenzo[c]quinolines and 1-hydroxyhexahydrobenzo[c]quinoline-9(8H)-ones as antiemetic agents |
| US4309545A (en) * | 1980-07-28 | 1982-01-05 | Pfizer Inc. | Oximino-1-hydroxyoctahydrobenzo[c]quinolines and derivatives thereof |
| US4406888A (en) * | 1981-01-09 | 1983-09-27 | Pfizer Inc. | Aqueous micellar solutions of levonantradol and N-methyllevonantradol and lyophilic forms thereof for reconstitution |
| HU194858B (en) * | 1982-12-03 | 1988-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing dibenzo/b,d/pirane derivatives and pharmaceutical compositions containing them |
| WO2010111436A2 (en) * | 2009-03-25 | 2010-09-30 | Abbott Laboratories | Antiviral compounds and uses thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636058A (en) * | 1966-03-25 | 1972-01-18 | Hoffmann La Roche | 7 10 - dihydro - 3 - alkyl - 6h - dibenzo(b d) pyran-6 9(8h)-diones and 5-hydroxy-7-alkyl-4-chromanones |
| US3507885A (en) * | 1966-03-25 | 1970-04-21 | Hoffmann La Roche | 3-alkyl-6h-dibenzo(b,d)pyrans |
| US3649650A (en) * | 1970-02-13 | 1972-03-14 | Little Inc A | Novel derivatives of tetrahydro-cannabinol |
| CA994791A (en) * | 1971-05-12 | 1976-08-10 | Louis S. Harris | Esters of benzopyrans |
| US3856821A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | ALKOXY DIBENZO (b,d) PYRANS |
| US3968125A (en) * | 1973-11-05 | 1976-07-06 | Eli Lilly And Company | Dihydroxyhexahydrodibenzo[b,d]pyrans |
| US3944673A (en) * | 1973-11-05 | 1976-03-16 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as analgesic drugs |
| US3928598A (en) * | 1973-11-05 | 1975-12-23 | Lilly Co Eli | Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug |
| GB1522057A (en) * | 1975-11-03 | 1978-08-23 | Pfizer | 9-hydroxydibenzo(b,d)pyrans and intermediates therefor |
-
1977
- 1977-04-25 SE SE7704749A patent/SE7704749L/en not_active Application Discontinuation
- 1977-05-13 DD DD7700198919A patent/DD130855A5/en unknown
- 1977-05-13 IL IL52087A patent/IL52087A/en unknown
- 1977-05-13 DE DE19772722383 patent/DE2722383A1/en active Granted
- 1977-05-13 CA CA278,410A patent/CA1095909A/en not_active Expired
- 1977-05-13 PH PH19772A patent/PH16833A/en unknown
- 1977-05-14 ES ES458812A patent/ES458812A1/en not_active Expired
- 1977-05-16 NZ NZ184114A patent/NZ184114A/en unknown
- 1977-05-16 GR GR53474A patent/GR74122B/el unknown
- 1977-05-16 LU LU77341A patent/LU77341A1/xx unknown
- 1977-05-16 DK DK212677A patent/DK212677A/en not_active Application Discontinuation
- 1977-05-16 CH CH610477A patent/CH626881A5/en not_active IP Right Cessation
- 1977-05-16 NO NO771738A patent/NO147028C/en unknown
- 1977-05-16 PT PT66550A patent/PT66550B/en unknown
- 1977-05-16 FI FI771550A patent/FI64141C/en not_active IP Right Cessation
- 1977-05-17 BG BG037712A patent/BG28415A4/en unknown
- 1977-05-17 BG BG037713A patent/BG28416A4/en unknown
- 1977-05-17 BG BG037711A patent/BG28414A4/en unknown
- 1977-05-17 JP JP52056068A patent/JPS6016426B2/en not_active Expired
- 1977-05-17 NL NLAANVRAGE7705433,A patent/NL170141C/en active
- 1977-05-17 BG BG036340A patent/BG27897A3/en unknown
- 1977-05-17 FR FR7715049A patent/FR2362129A1/en active Granted
- 1977-05-17 RO RO7796757A patent/RO76839A/en unknown
- 1977-05-17 AR AR267660A patent/AR215896A1/en active
-
1978
- 1978-04-26 NL NL7804461A patent/NL7804461A/en not_active Application Discontinuation
- 1978-04-27 ES ES469203A patent/ES469203A1/en not_active Expired
- 1978-04-27 ES ES469202A patent/ES469202A1/en not_active Expired
- 1978-04-27 ES ES469204A patent/ES469204A1/en not_active Expired
-
1980
- 1980-02-14 FR FR8003318A patent/FR2446284A1/en active Granted
- 1980-08-18 CH CH621980A patent/CH628034A5/en not_active IP Right Cessation
-
1981
- 1981-03-05 SU SU813254395A patent/SU1098520A3/en active
-
1982
- 1982-07-19 YU YU01568/82A patent/YU156882A/en unknown
- 1982-07-19 YU YU01569/82A patent/YU156982A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19981103 |