FI66368C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 6,1-dihydro-11-oxodibens(b e)oxepin-2-aettiksyraderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 6,1-dihydro-11-oxodibens(b e)oxepin-2-aettiksyraderivat Download PDFInfo
- Publication number
- FI66368C FI66368C FI2583/74A FI258374A FI66368C FI 66368 C FI66368 C FI 66368C FI 2583/74 A FI2583/74 A FI 2583/74A FI 258374 A FI258374 A FI 258374A FI 66368 C FI66368 C FI 66368C
- Authority
- FI
- Finland
- Prior art keywords
- dihydro
- oxepine
- oxodibenz
- ethyl
- acetic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- QFGMXJOBTNZHEL-UHFFFAOYSA-N isoxepac Chemical class O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 QFGMXJOBTNZHEL-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 239000002253 acid Substances 0.000 description 6
- -1 methanol or ethanol Chemical compound 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BCYWXPITXHFIQM-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]benzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=CC=C1C(O)=O BCYWXPITXHFIQM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YNZIKMGIXNMRAO-UHFFFAOYSA-N 2-(7-chloro-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=C(Cl)C=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 YNZIKMGIXNMRAO-UHFFFAOYSA-N 0.000 description 2
- RKHJWZBEIQMVGH-UHFFFAOYSA-N 2-(8-chloro-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=CC(Cl)=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 RKHJWZBEIQMVGH-UHFFFAOYSA-N 0.000 description 2
- ZLNSGZYOFZNWDE-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-5-chlorobenzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=C(Cl)C=C1C(O)=O ZLNSGZYOFZNWDE-UHFFFAOYSA-N 0.000 description 2
- CTXNHHIRBPGKQW-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-5-fluorobenzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=C(F)C=C1C(O)=O CTXNHHIRBPGKQW-UHFFFAOYSA-N 0.000 description 2
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- 238000010171 animal model Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- CXTGBNDIOWSNLD-UHFFFAOYSA-N ethyl 3-chloro-2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=C(Cl)C=CC=C1C(=O)OCC CXTGBNDIOWSNLD-UHFFFAOYSA-N 0.000 description 2
- JBOJNFIQZICKSZ-UHFFFAOYSA-N ethyl 4-chloro-2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC(Cl)=CC=C1C(=O)OCC JBOJNFIQZICKSZ-UHFFFAOYSA-N 0.000 description 2
- IEDKCDMWDDVNMJ-UHFFFAOYSA-N ethyl 5-chloro-2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC=C(Cl)C=C1C(=O)OCC IEDKCDMWDDVNMJ-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical class OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- XHRCNWPQPFZGPK-UHFFFAOYSA-N methyl 2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)OC)=CC=C21 XHRCNWPQPFZGPK-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
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- 239000003279 phenylacetic acid Substances 0.000 description 2
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- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- ZNEMGFATAVGQSF-UHFFFAOYSA-N 1-(2-amino-6,7-dihydro-4H-[1,3]thiazolo[4,5-c]pyridin-5-yl)-2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound NC=1SC2=C(CN(CC2)C(CC=2OC(=NN=2)C=2C=NC(=NC=2)NC2CC3=CC=CC=C3C2)=O)N=1 ZNEMGFATAVGQSF-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
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- ZMQDSLUBMRTEAX-UHFFFAOYSA-N ethyl 2-[[4-(1-ethoxy-1-oxopropan-2-yl)phenoxy]methyl]benzoate Chemical compound C1=CC(C(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1C(=O)OCC ZMQDSLUBMRTEAX-UHFFFAOYSA-N 0.000 description 1
- DUKSBWBJTZVOPF-UHFFFAOYSA-N ethyl 2-chloro-6-methylbenzoate Chemical compound CCOC(=O)C1=C(C)C=CC=C1Cl DUKSBWBJTZVOPF-UHFFFAOYSA-N 0.000 description 1
- SOUAXOGPALPTTC-UHFFFAOYSA-N ethyl 2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1C SOUAXOGPALPTTC-UHFFFAOYSA-N 0.000 description 1
- NLTONRXIPNPAGV-UHFFFAOYSA-N ethyl 4-chloro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1C NLTONRXIPNPAGV-UHFFFAOYSA-N 0.000 description 1
- RLCFHMSCTWXLTQ-UHFFFAOYSA-N ethyl 4-fluoro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(F)C=C1C RLCFHMSCTWXLTQ-UHFFFAOYSA-N 0.000 description 1
- UQFYMEQTOWLWHW-UHFFFAOYSA-N ethyl 5-chloro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC(Cl)=CC=C1C UQFYMEQTOWLWHW-UHFFFAOYSA-N 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- FSEZHVHHAAENBM-UHFFFAOYSA-N propan-2-yl 2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)OC(C)C)=CC=C21 FSEZHVHHAAENBM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39480173A | 1973-09-06 | 1973-09-06 | |
| US39480173 | 1973-09-06 | ||
| US05/459,774 US4585788A (en) | 1973-09-06 | 1974-04-10 | 6,11-dihydrodibenz[b,e]oxepin-acetic acids and derivatives |
| US45977474 | 1974-04-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI258374A7 FI258374A7 (en, 2012) | 1975-03-07 |
| FI66368B FI66368B (fi) | 1984-06-29 |
| FI66368C true FI66368C (fi) | 1984-10-10 |
Family
ID=27014870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2583/74A FI66368C (fi) | 1973-09-06 | 1974-09-04 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 6,1-dihydro-11-oxodibens(b e)oxepin-2-aettiksyraderivat |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4585788A (en, 2012) |
| JP (1) | JPS5058084A (en, 2012) |
| AT (1) | AT342053B (en, 2012) |
| AU (1) | AU499709B2 (en, 2012) |
| CA (1) | CA1153384A (en, 2012) |
| CH (2) | CH609960A5 (en, 2012) |
| DE (1) | DE2442060A1 (en, 2012) |
| DK (1) | DK470574A (en, 2012) |
| FI (1) | FI66368C (en, 2012) |
| FR (1) | FR2242976B1 (en, 2012) |
| GB (1) | GB1481866A (en, 2012) |
| IE (1) | IE39835B1 (en, 2012) |
| IL (1) | IL45585A (en, 2012) |
| NL (1) | NL7411565A (en, 2012) |
| NO (1) | NO142397C (en, 2012) |
| SE (1) | SE7411156L (en, 2012) |
| YU (2) | YU239574A (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56156273A (en) | 1980-03-31 | 1981-12-02 | Dainippon Pharmaceut Co Ltd | Acetic derivative |
| DE3125374A1 (de) * | 1981-06-27 | 1983-01-13 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von heteroaryl- und dibenzoxepinalkansaeuren |
| US4515946A (en) * | 1981-12-23 | 1985-05-07 | Hoechst-Roussel Pharmaceuticals Inc. | 6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives |
| US4576960A (en) * | 1981-12-23 | 1986-03-18 | Hoechst Roussel Pharmaceuticals Incorporated | 6,11-Dihydro-11-oxo-dibenz[b,e]oxepin derivatives |
| US4526891A (en) * | 1983-03-10 | 1985-07-02 | Hoechst Roussel Pharmaceuticals Inc. | Substituted alkyl amine derivatives of 6,11-dihydro-11-oxodibenz[b,e]oxepins |
| EP0188802A3 (en) * | 1984-12-26 | 1986-08-20 | Kyowa Hakko Kogyo Co., Ltd. | Dibenz (b,e) oxepin derivative and antiallergic agent |
| FR2580280B1 (fr) * | 1985-04-11 | 1987-05-22 | Synthelabo | Derives d'acide dibenzo(be)oxepinne-acetique, leur preparation et leur application en therapeutique |
| JPS6310784A (ja) * | 1986-03-03 | 1988-01-18 | Kyowa Hakko Kogyo Co Ltd | 抗アレルギー剤 |
| FR2608606B1 (fr) * | 1986-12-22 | 1989-03-10 | Synthelabo | Derives d'acide dibenzo(be)oxepinne-acetique, leur preparation et leur application en therapeutique |
| US4882351A (en) * | 1987-10-14 | 1989-11-21 | Roussel Uclaf | Tricyclic compounds |
| US4994463A (en) * | 1987-12-14 | 1991-02-19 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic thromboxane A2 antagonists |
| US5242931A (en) * | 1988-06-09 | 1993-09-07 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds as TXA2 antagonists |
| US4999363A (en) * | 1988-06-09 | 1991-03-12 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds |
| EP0436025A4 (en) * | 1988-09-20 | 1991-09-11 | Hisamitsu Pharmaceutical Co. Inc. | Novel dibenz b,e)oxepin derivatives |
| US5840749A (en) * | 1989-08-25 | 1998-11-24 | Hoechst Marion Roussel, Inc. | N-hydroxy-dibenz b,e!oxepinalkylamines, N-hydroxy-dibenz b,e!oxepinalkanoic acid amides and related heterocyclic analogues |
| TW209861B (en, 2012) * | 1989-08-25 | 1993-07-21 | Hoechst Roussel Pharma | |
| US5574173A (en) * | 1993-12-06 | 1996-11-12 | Schering Corporation | Tricyclic derivatives, compositions and methods of use |
| US6989462B2 (en) * | 2003-03-25 | 2006-01-24 | Sanofi-Aventis Deutschland Gmbh | Synthesis of 2-chloromethyl-6-methylbenzoic ester |
| US7687646B2 (en) * | 2006-03-28 | 2010-03-30 | Azad Pharmaceutical Ingredients, Ag | Polymorphic forms of olopatadine hydrochloride and methods for producing olopatadine and salts thereof |
| ES2399453T3 (es) * | 2006-08-21 | 2013-04-01 | Sumitomo Chemical Company Limited | Método para producir éster metílico del ácido 2-(4-toxicarbonilmetilfenoximetil)benzoico |
| CN101516865B (zh) * | 2006-10-02 | 2013-01-23 | 住友化学株式会社 | 氧代二苯并氧杂*乙酸的叔烷基酯 |
| JP5139016B2 (ja) * | 2006-10-02 | 2013-02-06 | 住友化学株式会社 | オキソジベンゾオキセピン酢酸第３級アルキルエステルの製造方法 |
| EP2145882B1 (en) * | 2008-07-16 | 2013-08-21 | Crystal Pharma, S.A.U. | Process for obtaining olopatadine and intermediates |
| CN106518833A (zh) * | 2015-09-15 | 2017-03-22 | 江苏吉贝尔药业股份有限公司 | 一种新的6，11-二氢-11-氧代二苯并［b，e］噁庚因-2-乙酸制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS47425Y1 (en, 2012) * | 1968-03-14 | 1972-01-10 | ||
| JPS48389Y1 (en, 2012) * | 1968-10-15 | 1973-01-08 | ||
| US3702852A (en) * | 1970-02-24 | 1972-11-14 | Squibb & Sons Inc | Carboxylated dibenzoxazepines and dibenzothiazepines |
| US3758528A (en) * | 1970-03-13 | 1973-09-11 | Science Union & Cie | Tricyclic compounds |
| US3714201A (en) * | 1970-11-24 | 1973-01-30 | Squibb & Sons Inc | 5,11-dihydrodibenzoxa(or thia) zepine derivatives |
-
1974
- 1974-04-10 US US05/459,774 patent/US4585788A/en not_active Expired - Lifetime
- 1974-08-30 NL NL7411565A patent/NL7411565A/xx not_active Application Discontinuation
- 1974-09-03 IL IL7445585A patent/IL45585A/en unknown
- 1974-09-03 CH CH675378A patent/CH609960A5/xx not_active IP Right Cessation
- 1974-09-03 DE DE2442060A patent/DE2442060A1/de not_active Withdrawn
- 1974-09-03 CH CH1195574A patent/CH615172A5/de not_active IP Right Cessation
- 1974-09-04 FI FI2583/74A patent/FI66368C/fi active
- 1974-09-04 AU AU72962/74A patent/AU499709B2/en not_active Expired
- 1974-09-04 SE SE7411156A patent/SE7411156L/xx unknown
- 1974-09-05 CA CA000208542A patent/CA1153384A/en not_active Expired
- 1974-09-05 DK DK470574A patent/DK470574A/da not_active Application Discontinuation
- 1974-09-05 NO NO74743203A patent/NO142397C/no unknown
- 1974-09-05 IE IE1847/74A patent/IE39835B1/xx unknown
- 1974-09-05 AT AT716474A patent/AT342053B/de not_active IP Right Cessation
- 1974-09-06 GB GB39112/74A patent/GB1481866A/en not_active Expired
- 1974-09-06 FR FR7430329A patent/FR2242976B1/fr not_active Expired
- 1974-09-06 JP JP49102876A patent/JPS5058084A/ja active Pending
- 1974-09-15 YU YU02395/74A patent/YU239574A/xx unknown
-
1980
- 1980-09-12 YU YU02338/80A patent/YU233880A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1153384A (en) | 1983-09-06 |
| DK470574A (en, 2012) | 1975-05-05 |
| AU499709B2 (en) | 1979-05-03 |
| SE7411156L (en, 2012) | 1975-03-07 |
| US4585788A (en) | 1986-04-29 |
| YU239574A (en) | 1982-06-18 |
| FR2242976B1 (en, 2012) | 1978-07-21 |
| JPS5058084A (en, 2012) | 1975-05-20 |
| ATA716474A (de) | 1977-07-15 |
| NO142397C (no) | 1980-08-13 |
| NO142397B (no) | 1980-05-05 |
| DE2442060A1 (de) | 1975-05-07 |
| AU7296274A (en) | 1976-04-15 |
| AT342053B (de) | 1978-03-10 |
| FR2242976A1 (en, 2012) | 1975-04-04 |
| NO743203L (en, 2012) | 1975-04-01 |
| CH615172A5 (en, 2012) | 1980-01-15 |
| IE39835B1 (en) | 1979-01-17 |
| FI258374A7 (en, 2012) | 1975-03-07 |
| FI66368B (fi) | 1984-06-29 |
| IL45585A (en) | 1977-06-30 |
| IL45585A0 (en) | 1974-11-29 |
| CH609960A5 (en, 2012) | 1979-03-30 |
| IE39835L (en) | 1975-03-06 |
| GB1481866A (en) | 1977-08-03 |
| YU233880A (en) | 1983-04-27 |
| NL7411565A (nl) | 1975-03-10 |
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