CA1125756A - Indane-acetic acid aminoesters, their preparation and their use in therapy - Google Patents
Indane-acetic acid aminoesters, their preparation and their use in therapyInfo
- Publication number
- CA1125756A CA1125756A CA331,498A CA331498A CA1125756A CA 1125756 A CA1125756 A CA 1125756A CA 331498 A CA331498 A CA 331498A CA 1125756 A CA1125756 A CA 1125756A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- process according
- compound
- acetic acid
- salt
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000002560 therapeutic procedure Methods 0.000 title abstract description 5
- OUODBMYUKUQGSR-UHFFFAOYSA-N amino 2-(2,3-dihydro-1h-inden-1-yl)acetate Chemical class C1=CC=C2C(CC(=O)ON)CCC2=C1 OUODBMYUKUQGSR-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 150000007513 acids Chemical class 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- -1 haloethyl ester Chemical class 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 150000004820 halides Chemical class 0.000 claims description 9
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 3
- BUVKILSTJGGJJN-UHFFFAOYSA-N acetic acid;2,3-dihydro-1h-indene Chemical compound CC(O)=O.C1=CC=C2CCCC2=C1 BUVKILSTJGGJJN-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 229940022682 acetone Drugs 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 229960001701 chloroform Drugs 0.000 description 11
- 229940076134 benzene Drugs 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 229960000443 hydrochloric acid Drugs 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- VTZRAFPPVSWWJU-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1h-inden-5-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=C2CC(CC)CC2=C1 VTZRAFPPVSWWJU-UHFFFAOYSA-N 0.000 description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
- 208000002193 Pain Diseases 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- YAGOIUXXHWBFPI-UHFFFAOYSA-N 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)propanoyl chloride Chemical compound C1=C(C(C)C(Cl)=O)C=C2CC(C(C)C)CC2=C1 YAGOIUXXHWBFPI-UHFFFAOYSA-N 0.000 description 3
- FWOZXAFACIHCGM-UHFFFAOYSA-N 2-bromoethyl 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)propanoate Chemical compound C1=C(C(C)C(=O)OCCBr)C=C2CC(C(C)C)CC2=C1 FWOZXAFACIHCGM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RYDUZJFCKYTEHX-UHFFFAOYSA-N 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=C2CC(C(C)C)CC2=C1 RYDUZJFCKYTEHX-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229940073584 methylene chloride Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- VNPHMIKNOXMWIV-UHFFFAOYSA-N 1-phenyl-3-(trifluoromethyl)piperazine hydrochloride Chemical compound Cl.C1CNC(C(F)(F)F)CN1C1=CC=CC=C1 VNPHMIKNOXMWIV-UHFFFAOYSA-N 0.000 description 1
- GQTXGYOQCPMYGO-UHFFFAOYSA-N 1-piperazin-1-yl-1-[3-(trifluoromethyl)phenyl]ethanol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(O)(C)N1CCNCC1 GQTXGYOQCPMYGO-UHFFFAOYSA-N 0.000 description 1
- VLYRRKUBQCUMOS-UHFFFAOYSA-N 1-piperazin-1-yl-1-[3-(trifluoromethyl)phenyl]ethanol;hydrochloride Chemical compound Cl.C=1C=CC(C(F)(F)F)=CC=1C(O)(C)N1CCNCC1 VLYRRKUBQCUMOS-UHFFFAOYSA-N 0.000 description 1
- ALCJUMGNAUUWSQ-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1h-inden-5-yl)propanoyl chloride Chemical compound C1=C(C(C)C(Cl)=O)C=C2CC(CC)CC2=C1 ALCJUMGNAUUWSQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WOZWHDSOMPCICU-UHFFFAOYSA-N 2-bromoethyl 2-(2-ethyl-2,3-dihydro-1h-inden-5-yl)propanoate Chemical compound C1=C(C(C)C(=O)OCCBr)C=C2CC(CC)CC2=C1 WOZWHDSOMPCICU-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000011102 Thera Species 0.000 description 1
- CLYFOWOXNDGKAY-UHFFFAOYSA-N [2-piperazin-1-yl-2-[3-(trifluoromethyl)phenyl]ethyl] 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)propanoate Chemical compound C1=C2CC(C(C)C)CC2=CC=C1C(C)C(=O)OCC(C=1C=C(C=CC=1)C(F)(F)F)N1CCNCC1 CLYFOWOXNDGKAY-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- 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
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7821849 | 1978-07-24 | ||
| FR7821849A FR2432021A1 (fr) | 1978-07-24 | 1978-07-24 | Nouveaux esters amines d'acide indane-acetique et leur utilisation en therapeutique |
| FR7913532A FR2457862A2 (fr) | 1979-05-28 | 1979-05-28 | Procede de preparation d'esters amines d'acide indaneacetique |
| FR7913532 | 1979-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125756A true CA1125756A (en) | 1982-06-15 |
Family
ID=26220683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA331,498A Expired CA1125756A (en) | 1978-07-24 | 1979-07-10 | Indane-acetic acid aminoesters, their preparation and their use in therapy |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4271161A (en, 2012) |
| EP (2) | EP0008256A3 (en, 2012) |
| AR (2) | AR220210A1 (en, 2012) |
| AU (1) | AU516742B2 (en, 2012) |
| CA (1) | CA1125756A (en, 2012) |
| ES (2) | ES482656A0 (en, 2012) |
| GB (3) | GB2038830A (en, 2012) |
| GR (1) | GR65999B (en, 2012) |
| PH (1) | PH14387A (en, 2012) |
| PT (1) | PT69941A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4339580A (en) * | 1979-06-26 | 1982-07-13 | Mitsubishi Chemical Industries, Limited | Piperazinylalkoxyindanes and acid addition salts thereof |
| DE3377415D1 (en) * | 1983-11-09 | 1988-08-25 | Juste Sa | Novel phenylpiperazine derivatives, process for preparing them and therapeutic compositions containing them |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2258840A1 (en) * | 1974-01-29 | 1975-08-22 | Synthelabo | (4-Phenylpiperazino) alkyl esters - with analgesic activity for human and veterinary use |
| GB1437868A (en) * | 1973-05-09 | 1976-06-03 | Synthelabo | Arylpiperazinoalkyl esters |
| AR206619A1 (es) | 1974-02-07 | 1976-08-06 | Hexachimie | Procedimiento para peparar acidos 5-indanilaceticos |
| FR2341313A1 (fr) * | 1976-02-23 | 1977-09-16 | Roussel Uclaf | Nouvelles quinoleines substituees, leur procede de preparation et leur application comme medicament |
| SE7712447L (sv) * | 1977-01-21 | 1978-07-22 | Roussel Uclaf | Sett att framstella nya bensofenonderivat |
-
1979
- 1979-06-09 GR GR59316A patent/GR65999B/el unknown
- 1979-07-03 GB GB8002206A patent/GB2038830A/en not_active Withdrawn
- 1979-07-03 GB GB7923195A patent/GB2027019B/en not_active Expired
- 1979-07-03 GB GB08210290A patent/GB2103599B/en not_active Expired
- 1979-07-06 AR AR277223A patent/AR220210A1/es active
- 1979-07-09 US US06/055,907 patent/US4271161A/en not_active Expired - Lifetime
- 1979-07-10 CA CA331,498A patent/CA1125756A/en not_active Expired
- 1979-07-13 EP EP79400500A patent/EP0008256A3/fr not_active Withdrawn
- 1979-07-13 EP EP81103269A patent/EP0034838A3/fr not_active Withdrawn
- 1979-07-18 AU AU49019/79A patent/AU516742B2/en not_active Ceased
- 1979-07-18 PT PT69941A patent/PT69941A/pt unknown
- 1979-07-19 ES ES482656A patent/ES482656A0/es active Granted
- 1979-07-23 PH PH22804A patent/PH14387A/en unknown
-
1980
- 1980-06-02 ES ES492085A patent/ES492085A0/es active Granted
- 1980-08-26 AR AR282297A patent/AR220500A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| GR65999B (en, 2012) | 1981-01-13 |
| PT69941A (fr) | 1979-08-01 |
| GB2103599B (en) | 1983-06-08 |
| ES8104254A1 (es) | 1981-04-16 |
| US4271161A (en) | 1981-06-02 |
| EP0034838A2 (fr) | 1981-09-02 |
| ES8101063A1 (es) | 1980-12-01 |
| AR220210A1 (es) | 1980-10-15 |
| EP0008256A2 (fr) | 1980-02-20 |
| GB2027019A (en) | 1980-02-13 |
| GB2103599A (en) | 1983-02-23 |
| AR220500A1 (es) | 1980-10-31 |
| EP0034838A3 (fr) | 1981-10-07 |
| EP0008256A3 (fr) | 1980-12-10 |
| PH14387A (en) | 1981-06-24 |
| GB2027019B (en) | 1983-01-06 |
| ES482656A0 (es) | 1980-12-01 |
| GB2038830A (en) | 1980-07-30 |
| ES492085A0 (es) | 1981-04-16 |
| AU4901979A (en) | 1980-01-31 |
| AU516742B2 (en) | 1981-06-18 |
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