CA1076139A - Method of producing indan derivatives - Google Patents
Method of producing indan derivativesInfo
- Publication number
- CA1076139A CA1076139A CA268,042A CA268042A CA1076139A CA 1076139 A CA1076139 A CA 1076139A CA 268042 A CA268042 A CA 268042A CA 1076139 A CA1076139 A CA 1076139A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- mixture
- compound
- reaction
- general 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
- 238000000034 method Methods 0.000 title claims description 28
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical class C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 title claims description 21
- -1 sulfonyl-methylisonitrile compound Chemical class 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- 239000000284 extract Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- GREYVSOWISPLEK-UHFFFAOYSA-N 4-(4-methylbenzoyl)-2,3-dihydroinden-1-one Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC2=C1CCC2=O GREYVSOWISPLEK-UHFFFAOYSA-N 0.000 description 2
- BAZOIHGIIQZVEN-UHFFFAOYSA-N 4-benzoyl-2,3-dihydroinden-1-one Chemical compound C=1C=CC=2C(=O)CCC=2C=1C(=O)C1=CC=CC=C1 BAZOIHGIIQZVEN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- AMECRMCTYSTXNV-UHFFFAOYSA-N isocyano(sulfonyl)methane Chemical compound O=S(=O)=C[N+]#[C-] AMECRMCTYSTXNV-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BBRYSETUUIQILU-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-yl-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1C2=CC=CC=C2CC1 BBRYSETUUIQILU-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- FDRLLMAFDMQAJY-UHFFFAOYSA-N 4-(4-chlorobenzoyl)-2,3-dihydroinden-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC2=C1CCC2=O FDRLLMAFDMQAJY-UHFFFAOYSA-N 0.000 description 1
- WZAJBIXBRFTJRC-UHFFFAOYSA-N 4-(4-methylbenzoyl)-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC2=C1CCC2C(O)=O WZAJBIXBRFTJRC-UHFFFAOYSA-N 0.000 description 1
- FXUBHWHRMVGJOG-UHFFFAOYSA-N 4-benzoyl-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound OC(=O)C1CCC2=C1C=CC=C2C(=O)C1=CC=CC=C1 FXUBHWHRMVGJOG-UHFFFAOYSA-N 0.000 description 1
- OXKUWKMVTHKKBG-UHFFFAOYSA-N 6-chloro-5-cyclohexyl-2,3-dihydroinden-1-one Chemical compound ClC1=CC=2C(=O)CCC=2C=C1C1CCCCC1 OXKUWKMVTHKKBG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 102100029469 WD repeat and HMG-box DNA-binding protein 1 Human genes 0.000 description 1
- 101710097421 WD repeat and HMG-box DNA-binding protein 1 Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50152358A JPS6012341B2 (ja) | 1975-12-19 | 1975-12-19 | インダン誘導体の製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076139A true CA1076139A (en) | 1980-04-22 |
Family
ID=15538786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA268,042A Expired CA1076139A (en) | 1975-12-19 | 1976-12-16 | Method of producing indan derivatives |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS6012341B2 (xx) |
| AT (1) | AT346837B (xx) |
| AU (1) | AU505609B2 (xx) |
| BE (1) | BE849561A (xx) |
| CA (1) | CA1076139A (xx) |
| CH (1) | CH603534A5 (xx) |
| DE (1) | DE2656784A1 (xx) |
| DK (1) | DK568476A (xx) |
| ES (1) | ES454292A1 (xx) |
| FI (1) | FI62049C (xx) |
| FR (1) | FR2336371A1 (xx) |
| GB (1) | GB1537906A (xx) |
| GR (1) | GR62073B (xx) |
| HU (1) | HU171842B (xx) |
| MX (1) | MX3741E (xx) |
| NL (1) | NL7614110A (xx) |
| NO (1) | NO764290L (xx) |
| SE (1) | SE419213B (xx) |
| SU (1) | SU667127A3 (xx) |
| ZA (1) | ZA767225B (xx) |
-
1975
- 1975-12-19 JP JP50152358A patent/JPS6012341B2/ja not_active Expired
-
1976
- 1976-12-03 ZA ZA767225A patent/ZA767225B/xx unknown
- 1976-12-07 AT AT905576A patent/AT346837B/de not_active IP Right Cessation
- 1976-12-08 MX MX765197U patent/MX3741E/es unknown
- 1976-12-13 HU HU76TA00001420A patent/HU171842B/hu unknown
- 1976-12-13 GB GB51889/76A patent/GB1537906A/en not_active Expired
- 1976-12-14 AU AU20553/76A patent/AU505609B2/en not_active Expired
- 1976-12-14 GR GR52398A patent/GR62073B/el unknown
- 1976-12-15 DE DE19762656784 patent/DE2656784A1/de not_active Withdrawn
- 1976-12-16 ES ES454292A patent/ES454292A1/es not_active Expired
- 1976-12-16 CA CA268,042A patent/CA1076139A/en not_active Expired
- 1976-12-16 SE SE7614169A patent/SE419213B/xx unknown
- 1976-12-17 FR FR7638182A patent/FR2336371A1/fr active Granted
- 1976-12-17 NO NO764290A patent/NO764290L/no unknown
- 1976-12-17 BE BE173403A patent/BE849561A/xx not_active IP Right Cessation
- 1976-12-17 NL NL7614110A patent/NL7614110A/xx not_active Application Discontinuation
- 1976-12-17 DK DK568476A patent/DK568476A/da unknown
- 1976-12-17 SU SU762429706A patent/SU667127A3/ru active
- 1976-12-17 CH CH1594676A patent/CH603534A5/xx not_active IP Right Cessation
- 1976-12-17 FI FI763625A patent/FI62049C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1537906A (en) | 1979-01-10 |
| DK568476A (da) | 1977-06-20 |
| SU667127A3 (ru) | 1979-06-05 |
| HU171842B (hu) | 1978-03-28 |
| MX3741E (es) | 1981-06-05 |
| FI763625A (xx) | 1977-06-20 |
| NO764290L (xx) | 1977-06-21 |
| ZA767225B (en) | 1977-11-30 |
| ES454292A1 (es) | 1977-12-16 |
| FR2336371B1 (xx) | 1980-05-16 |
| FR2336371A1 (fr) | 1977-07-22 |
| CH603534A5 (xx) | 1978-08-31 |
| SE419213B (sv) | 1981-07-20 |
| AT346837B (de) | 1978-11-27 |
| FI62049B (fi) | 1982-07-30 |
| ATA905576A (de) | 1978-04-15 |
| JPS6012341B2 (ja) | 1985-04-01 |
| FI62049C (fi) | 1982-11-10 |
| AU2055376A (en) | 1978-06-22 |
| BE849561A (fr) | 1977-06-17 |
| NL7614110A (nl) | 1977-06-21 |
| SE7614169L (sv) | 1977-06-20 |
| AU505609B2 (en) | 1979-11-29 |
| JPS5277044A (en) | 1977-06-29 |
| DE2656784A1 (de) | 1977-06-30 |
| GR62073B (en) | 1979-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPWO2006006496A1 (ja) | アズレン誘導体の製造方法及びその合成中間体 | |
| CH647520A5 (fr) | Derives du nortropane, leur procede de preparation et composition pharmaceutique les contenant. | |
| CA2450313C (en) | Process for the production of the piperidine derivative fexofenadine | |
| JPH06511256A (ja) | フルニクシンとその中間物質の製造方法 | |
| BRPI0721386A2 (pt) | processo para a preparaÇço de 2-substituÍdas -5-(1-alquiltio) alquil-piridinas | |
| CA1076139A (en) | Method of producing indan derivatives | |
| EP0990647B1 (en) | Process for producing quinolone derivatives | |
| JP2820739B2 (ja) | カルボスチリル誘導体の製造法 | |
| JPH01156965A (ja) | チオヒダントイン化合物 | |
| US6031103A (en) | Process for manufacturing 1-[3-cyclopentyl -2(R)-[1(R)-hydroxycarbamoyl)-2-(3, 4, 4-trimethyl -2, 5-D ioxo-1-imidazolidinyl) ethyl] propionyl] piperidine | |
| JP3810858B2 (ja) | ４−トリフルオロメチルニコチン酸の製造方法 | |
| EP0977723A1 (en) | Process for the preparation of trifluoroethoxyarenecarboxylic acids | |
| CA2221641A1 (en) | Improved process for preparing 4-hydroxy-2-pyrrolidone | |
| ES2212845T3 (es) | Procedimiento para la preparacion de 2-hidroxialquil-halofenonas. | |
| US4891433A (en) | Process for the preparation of dibenzothiepin derivative | |
| KR800000623B1 (ko) | 인단 유도체의 제조법 | |
| CA2183426A1 (en) | Process for producing 3-isoxazolecarboxylic acid | |
| JPH069625A (ja) | ４−ピリミジノン類の新規製造法 | |
| WO2006059345A2 (en) | Process for the preparation of acetylenic retinoid | |
| JP2512958B2 (ja) | １−ビフェニリルエタノ―ル誘導体およびその製法 | |
| JP2536756B2 (ja) | ５−アルコキシアントラニル酸エステル | |
| CA1285571C (en) | Anisole derivatives | |
| JP3058399B2 (ja) | ［［４−置換アセチル−ｏ−フェニレン］ジオキシ］ジ酢酸誘導体及びその製造方法 | |
| JPS6210500B2 (xx) | ||
| US4001224A (en) | 4-substituted-2, 3-dihydro-1-benzoxepin-3, 5-diones and tautomers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |