ES469204A1 - Novel benzo *c* quinolines - Google Patents
Novel benzo *c* quinolinesInfo
- Publication number
- ES469204A1 ES469204A1 ES469204A ES469204A ES469204A1 ES 469204 A1 ES469204 A1 ES 469204A1 ES 469204 A ES469204 A ES 469204A ES 469204 A ES469204 A ES 469204A ES 469204 A1 ES469204 A1 ES 469204A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- hydrogen
- integer
- see formula
- 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
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 125000005605 benzo group Chemical group 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 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 150000002431 hydrogen Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 3
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- -1 pyrrolo Chemical group 0.000 abstract 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 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
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical class C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 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)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Anesthesiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A process for the preparation of benzo (c) quinolines useful as agents for the central nervous system and having the formula **(See formula)** where A is **(See formula)** and the pharmaceutically acceptable acid addition salt of the compounds where A is I', where R is alkanoyloxy having from one to five carbon or hydroxymethyl atoms; R'is alkanoyloxy having one to five carbon atoms; hydroxymethyl; oxo, methylene, or alkylenedioxy having two to four carbon atoms; R1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or -CO- (CH2) p-NR2R3 where p is 0 or an integer from 1 to 4; each of R2 and R3 when taken individually is the same or different and is hydrogen or alkyl having from one to four carbon atoms; and R2 and R3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring, said ring being piperidino, pyrrolo, pyrrolidino, morpholino or N-alkylpiperazino having one to four carbon atoms in it. alkyl group; R4 is hydrogen, alkyl having 1 to 6 carbon atoms or - (CH2) z-C6H5 where z is an integer from 1 to 4; R5 is hydrogen, methyl or ethyl; -0-alkylene-0- is alkylenedioxy having two to four carbon atoms; R6 is hydrogen, - (CH2) y-carbalkoxy having from one to four carbon atoms in the alkoxy group and where y is 0 or an integer from 1 to 4, carbobenzyloxy, formyl, alkanoyl having from two to five atoms carbon, alkyl having from one to six carbon atoms; - (CH2) x-C6H5 where x is an integer from 1 to 4; or -C0 (CH2) x-1-C6H5; Z is alkylene having one to nine carbon atoms; or - (alk1) mX- (alk2) n- where each of (alk1) and (alk2) is the same or different and is alkylene having one to nine carbon atoms, provided that the sum of atoms of carbon in (alk1) plus (alk2) is not greater than nine, each of m and n is 0 or 1; and X is O, S, SO, or SO2; and W is hydrogen, methyl, pyridyl, piperidyl, (see formula) where W1 is hydrogen, fluorine, or (see formula) where W2 is hydrogen or (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; characterized by reducing a compound of Formula XX where A is **(See formula)** or an acylated derivative thereof where R1, R4, R5, R6, Z and W are as defined above, and if desired, before or after reduction, acylate a compound of Formula XX where A is **(See formula)** where R0 is oxo, methylene, or alkylenedioxy having two to four carbon atoms, or A is III'or IV'. (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 |
|---|---|
| ES469204A1 true ES469204A1 (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 |
| ES469202A Expired ES469202A1 (en) | 1976-05-17 | 1978-04-27 | Novel benzo *c* quinolines |
| ES469203A Expired ES469203A1 (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 (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES458812A Expired ES458812A1 (en) | 1976-05-17 | 1977-05-14 | Novel benzo *c* quinolines |
| ES469202A Expired ES469202A1 (en) | 1976-05-17 | 1978-04-27 | Novel benzo *c* quinolines |
| ES469203A Expired ES469203A1 (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) | BG28414A4 (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) | YU156982A (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 |
| CN102448920B (en) | 2009-03-25 | 2016-04-06 | Abbvie公司 | Antiviral compound and its purposes |
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 IL IL52087A patent/IL52087A/en unknown
- 1977-05-13 PH PH19772A patent/PH16833A/en unknown
- 1977-05-13 CA CA278,410A patent/CA1095909A/en not_active Expired
- 1977-05-13 DD DD7700198919A patent/DD130855A5/en unknown
- 1977-05-13 DE DE19772722383 patent/DE2722383A1/en active Granted
- 1977-05-14 ES ES458812A patent/ES458812A1/en not_active Expired
- 1977-05-16 PT PT66550A patent/PT66550B/en unknown
- 1977-05-16 DK DK212677A patent/DK212677A/en not_active Application Discontinuation
- 1977-05-16 NO NO771738A patent/NO147028C/en unknown
- 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 CH CH610477A patent/CH626881A5/en not_active IP Right Cessation
- 1977-05-16 FI FI771550A patent/FI64141C/en not_active IP Right Cessation
- 1977-05-17 AR AR267660A patent/AR215896A1/en active
- 1977-05-17 BG BG037711A patent/BG28414A4/en unknown
- 1977-05-17 NL NLAANVRAGE7705433,A patent/NL170141C/en active
- 1977-05-17 BG BG037712A patent/BG28415A4/en unknown
- 1977-05-17 BG BG037713A patent/BG28416A4/en unknown
- 1977-05-17 BG BG036340A patent/BG27897A3/en unknown
- 1977-05-17 JP JP52056068A patent/JPS6016426B2/en not_active Expired
- 1977-05-17 RO RO7796757A patent/RO76839A/en unknown
- 1977-05-17 FR FR7715049A patent/FR2362129A1/en active Granted
-
1978
- 1978-04-26 NL NL7804461A patent/NL7804461A/en not_active Application Discontinuation
- 1978-04-27 ES ES469202A patent/ES469202A1/en not_active Expired
- 1978-04-27 ES ES469203A patent/ES469203A1/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 YU01569/82A patent/YU156982A/en unknown
- 1982-07-19 YU YU01568/82A patent/YU156882A/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19981103 |