FI84824C - Analogifoerfarande foer framstaellning pao immunitetet inverkande 6- substituerade 6h-dibenzo/b,d/pyranderivat. - Google Patents
Analogifoerfarande foer framstaellning pao immunitetet inverkande 6- substituerade 6h-dibenzo/b,d/pyranderivat. Download PDFInfo
- Publication number
- FI84824C FI84824C FI813144A FI813144A FI84824C FI 84824 C FI84824 C FI 84824C FI 813144 A FI813144 A FI 813144A FI 813144 A FI813144 A FI 813144A FI 84824 C FI84824 C FI 84824C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- dibenzo
- pyran
- compounds
- Prior art date
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- 230000036039 immunity Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 83
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 9
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical group C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000007268 Pschorr arylation reaction Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 23
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- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- -1 carboxyethyl group Chemical group 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
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- 238000000034 method Methods 0.000 description 12
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- 238000002360 preparation method Methods 0.000 description 7
- OXJRPIUEFMWVOI-UHFFFAOYSA-N 2-(dimethylamino)ethyl 6h-benzo[c]chromene-6-carboxylate;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)OCCN(C)C)OC3=CC=CC=C3C2=C1 OXJRPIUEFMWVOI-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
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- 210000000601 blood cell Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
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- 231100000515 lung injury Toxicity 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
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- 210000003372 endocrine gland Anatomy 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
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- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- 239000006072 paste Substances 0.000 description 1
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- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 229920001592 potato starch Polymers 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
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- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8033774 | 1980-10-20 | ||
| GB8033774 | 1980-10-20 | ||
| GB8127718 | 1981-09-14 | ||
| GB8127718 | 1981-09-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI813144L FI813144L (fi) | 1982-04-21 |
| FI84824B FI84824B (fi) | 1991-10-15 |
| FI84824C true FI84824C (fi) | 1992-01-27 |
Family
ID=26277272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI813144A FI84824C (fi) | 1980-10-20 | 1981-10-12 | Analogifoerfarande foer framstaellning pao immunitetet inverkande 6- substituerade 6h-dibenzo/b,d/pyranderivat. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4463001A (en, 2012) |
| AT (1) | AT380245B (en, 2012) |
| AU (1) | AU542121B2 (en, 2012) |
| CA (1) | CA1235703A (en, 2012) |
| CH (1) | CH651302A5 (en, 2012) |
| DE (1) | DE3141387A1 (en, 2012) |
| DK (1) | DK154974C (en, 2012) |
| FI (1) | FI84824C (en, 2012) |
| FR (1) | FR2492378B1 (en, 2012) |
| HK (1) | HK9186A (en, 2012) |
| IL (1) | IL64008A (en, 2012) |
| IT (1) | IT1168040B (en, 2012) |
| MY (1) | MY8600398A (en, 2012) |
| NL (1) | NL191562C (en, 2012) |
| SE (1) | SE452009B (en, 2012) |
| SU (1) | SU1318163A3 (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2512024A1 (fr) * | 1981-08-27 | 1983-03-04 | Adir | Ethers tricycliques, leur preparation et les compositions pharmaceutiques les contenant |
| GB8505756D0 (en) * | 1985-03-06 | 1985-04-11 | Erba Farmitalia | Tricyclic dibenzo condensed derivatives |
| US5100909A (en) * | 1988-07-25 | 1992-03-31 | The Upjohn Company | Acetylenic imidazoles having central nervous system activity |
| US5180736A (en) * | 1989-03-23 | 1993-01-19 | Warner-Lambert Company | Polycyclic amines useful as cerebrovascular agents |
| US5202446A (en) * | 1990-05-23 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Fluoridated monomers based on 9-phenyl-9-perfluoroalkylxanthene |
| EP0757988A4 (en) * | 1994-04-27 | 2000-07-26 | Nippon Soda Co | IMIDAZOLE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME |
| ES2131020B1 (es) * | 1997-10-13 | 2000-03-01 | Lacer Sa | Derivados de benzofurano, dihidrobenzofunaro, dihidrobenzopirano y benzopirano como agentes antidepresivos. |
| CN110092769B (zh) * | 2018-01-30 | 2022-09-20 | 华东师范大学 | 一种色烯衍生物及其合成方法和应用 |
| JP2024503753A (ja) | 2021-01-27 | 2024-01-26 | ヴァンドリア エスアー | ウロリチン誘導体及びその使用方法 |
| CN118812482B (zh) * | 2024-06-24 | 2025-02-07 | 中国水产科学研究院长江水产研究所 | 一种4H-苯并[b]吡喃类衍生物B78及其在抗中华鳖虹彩病毒上的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799946A (en) * | 1972-03-13 | 1974-03-26 | Smithkline Corp | Dibenzo(b,d)pyran compounds |
| US3856822A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | 3-alkenyl dibenzo (b,d)pyrans |
| GB1464695A (en) * | 1974-06-24 | 1977-02-16 | Smithkline Corp | Dibenzo-b,c-pyrans and pharmaceutical compositions thereof |
-
1981
- 1981-10-01 US US06/307,597 patent/US4463001A/en not_active Expired - Lifetime
- 1981-10-06 IL IL64008A patent/IL64008A/xx not_active IP Right Cessation
- 1981-10-08 AU AU76161/81A patent/AU542121B2/en not_active Ceased
- 1981-10-12 FI FI813144A patent/FI84824C/fi not_active IP Right Cessation
- 1981-10-17 DE DE19813141387 patent/DE3141387A1/de active Granted
- 1981-10-19 DK DK461381A patent/DK154974C/da active
- 1981-10-19 CA CA000388273A patent/CA1235703A/en not_active Expired
- 1981-10-19 CH CH6665/81A patent/CH651302A5/de not_active IP Right Cessation
- 1981-10-19 SE SE8106167A patent/SE452009B/sv not_active IP Right Cessation
- 1981-10-19 IT IT24552/81A patent/IT1168040B/it active
- 1981-10-19 SU SU813346602A patent/SU1318163A3/ru active
- 1981-10-20 FR FR8119685A patent/FR2492378B1/fr not_active Expired
- 1981-10-20 NL NL8104749A patent/NL191562C/xx not_active IP Right Cessation
- 1981-10-20 AT AT0448781A patent/AT380245B/de not_active IP Right Cessation
-
1986
- 1986-02-05 HK HK91/86A patent/HK9186A/xx not_active IP Right Cessation
- 1986-12-30 MY MY398/86A patent/MY8600398A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK9186A (en) | 1986-02-14 |
| IT1168040B (it) | 1987-05-20 |
| DK154974C (da) | 1989-06-12 |
| DK154974B (da) | 1989-01-16 |
| FI84824B (fi) | 1991-10-15 |
| ATA448781A (de) | 1985-09-15 |
| IL64008A0 (en) | 1982-01-31 |
| FR2492378A1 (fr) | 1982-04-23 |
| SE8106167L (sv) | 1982-06-02 |
| AU7616181A (en) | 1982-09-09 |
| NL191562C (nl) | 1995-09-19 |
| FI813144L (fi) | 1982-04-21 |
| DK461381A (da) | 1982-04-21 |
| SU1318163A3 (ru) | 1987-06-15 |
| NL8104749A (nl) | 1982-05-17 |
| IT8124552A0 (it) | 1981-10-19 |
| MY8600398A (en) | 1986-12-31 |
| AU542121B2 (en) | 1985-02-07 |
| IL64008A (en) | 1986-07-31 |
| CH651302A5 (de) | 1985-09-13 |
| AT380245B (de) | 1986-04-25 |
| DE3141387A1 (de) | 1982-08-12 |
| CA1235703A (en) | 1988-04-26 |
| SE452009B (sv) | 1987-11-09 |
| DE3141387C2 (en, 2012) | 1991-05-02 |
| US4463001A (en) | 1984-07-31 |
| FR2492378B1 (fr) | 1985-06-28 |
| NL191562B (nl) | 1995-05-16 |
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