FR2478640A1 - Nouvelles thieno (2,3-d) pyridazinones-4 et thieno (2,3-d) pyridazinones-7, leur procede de preparation et leur therapeutique - Google Patents
Nouvelles thieno (2,3-d) pyridazinones-4 et thieno (2,3-d) pyridazinones-7, leur procede de preparation et leur therapeutique Download PDFInfo
- Publication number
- FR2478640A1 FR2478640A1 FR8006475A FR8006475A FR2478640A1 FR 2478640 A1 FR2478640 A1 FR 2478640A1 FR 8006475 A FR8006475 A FR 8006475A FR 8006475 A FR8006475 A FR 8006475A FR 2478640 A1 FR2478640 A1 FR 2478640A1
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- preparation
- carboxylic acid
- derivative
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Links
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 12
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 title claims abstract description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 title abstract description 10
- ZKHLBCVFVQJMBT-UHFFFAOYSA-N 3-benzoylthiophene-2-carboxylic acid Chemical compound S1C=CC(C(=O)C=2C=CC=CC=2)=C1C(=O)O ZKHLBCVFVQJMBT-UHFFFAOYSA-N 0.000 title description 3
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 150000004715 keto acids Chemical class 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 9
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims 2
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- 150000002367 halogens Chemical class 0.000 claims 1
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- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
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- -1 hydroyl Chemical group 0.000 description 25
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 239000000243 solution Substances 0.000 description 17
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 3
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- 239000012286 potassium permanganate Substances 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C1)(CCCC*(*)*1[C@](C1)(CCC2)I*)C1(*)CC2C(CCC*OCC*=C)O* Chemical compound CC(C1)(CCCC*(*)*1[C@](C1)(CCC2)I*)C1(*)CC2C(CCC*OCC*=C)O* 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
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- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
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- RWXRLARIZRNEDT-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]-5H-thieno[2,3-d]pyridazin-4-one Chemical compound FC(C=1C=C(C=CC=1)C1=CC2=C(C=NNC2=O)S1)(F)F RWXRLARIZRNEDT-UHFFFAOYSA-N 0.000 description 1
- FGJUGEQAUPANNZ-UHFFFAOYSA-N 2-benzoylthiophene-3-carboxylic acid Chemical compound C1=CSC(C(=O)C=2C=CC=CC=2)=C1C(=O)O FGJUGEQAUPANNZ-UHFFFAOYSA-N 0.000 description 1
- MZJHBUKIOBJCAW-UHFFFAOYSA-N 2-chloro-n,n-diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1Cl MZJHBUKIOBJCAW-UHFFFAOYSA-N 0.000 description 1
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- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- 108010010803 Gelatin Proteins 0.000 description 1
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- JLNGEXDJAQASHD-UHFFFAOYSA-N N,N-Diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1 JLNGEXDJAQASHD-UHFFFAOYSA-N 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- PUZORFQMRDHKBT-UHFFFAOYSA-N n,n-diethyl-4-methylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=C(C)C=C1 PUZORFQMRDHKBT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8006475A FR2478640A1 (fr) | 1980-03-24 | 1980-03-24 | Nouvelles thieno (2,3-d) pyridazinones-4 et thieno (2,3-d) pyridazinones-7, leur procede de preparation et leur therapeutique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8006475A FR2478640A1 (fr) | 1980-03-24 | 1980-03-24 | Nouvelles thieno (2,3-d) pyridazinones-4 et thieno (2,3-d) pyridazinones-7, leur procede de preparation et leur therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2478640A1 true FR2478640A1 (fr) | 1981-09-25 |
| FR2478640B1 FR2478640B1 (OSRAM) | 1983-04-22 |
Family
ID=9240002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8006475A Granted FR2478640A1 (fr) | 1980-03-24 | 1980-03-24 | Nouvelles thieno (2,3-d) pyridazinones-4 et thieno (2,3-d) pyridazinones-7, leur procede de preparation et leur therapeutique |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2478640A1 (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0243071A3 (en) * | 1986-04-22 | 1988-03-23 | Riker Laboratories, Inc. | Di-t-butylphenols substituted by a thenoyl group |
| WO1991012251A1 (fr) * | 1990-02-19 | 1991-08-22 | Chugai Seiyaku Kabushiki Kaisha | Nouveau compose heterocyclique condense et agent anti-asthme prepare a partir de ce compose |
| WO1999029695A1 (en) * | 1997-12-05 | 1999-06-17 | Astrazeneca Uk Limited | Novel compounds |
| US9296741B2 (en) | 2011-12-30 | 2016-03-29 | Abbvie Inc. | Bromodomain inhibitors |
| US10633379B2 (en) | 2016-04-15 | 2020-04-28 | Abbvie Inc. | Bromodomain inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3222365A (en) * | 1962-01-15 | 1965-12-07 | Lilly Co Eli | 4-halophenyl-2-alkyl-1(2)-phthalazinones |
| FR1453897A (fr) * | 1965-06-16 | 1966-07-22 | Dérivés du thiophène et de thiéno pyridazines |
-
1980
- 1980-03-24 FR FR8006475A patent/FR2478640A1/fr active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3222365A (en) * | 1962-01-15 | 1965-12-07 | Lilly Co Eli | 4-halophenyl-2-alkyl-1(2)-phthalazinones |
| FR1453897A (fr) * | 1965-06-16 | 1966-07-22 | Dérivés du thiophène et de thiéno pyridazines |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0243071A3 (en) * | 1986-04-22 | 1988-03-23 | Riker Laboratories, Inc. | Di-t-butylphenols substituted by a thenoyl group |
| WO1991012251A1 (fr) * | 1990-02-19 | 1991-08-22 | Chugai Seiyaku Kabushiki Kaisha | Nouveau compose heterocyclique condense et agent anti-asthme prepare a partir de ce compose |
| WO1999029695A1 (en) * | 1997-12-05 | 1999-06-17 | Astrazeneca Uk Limited | Novel compounds |
| US6342601B1 (en) | 1997-12-05 | 2002-01-29 | Astrazeneca Ab | Compounds |
| US6770646B2 (en) | 1997-12-05 | 2004-08-03 | Astrazeneca Ab | Substituted fused pyridazinone compounds; composition and use thereof |
| US9296741B2 (en) | 2011-12-30 | 2016-03-29 | Abbvie Inc. | Bromodomain inhibitors |
| US10633379B2 (en) | 2016-04-15 | 2020-04-28 | Abbvie Inc. | Bromodomain inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2478640B1 (OSRAM) | 1983-04-22 |
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