NO118710B - - Google Patents
Download PDFInfo
- Publication number
- NO118710B NO118710B NO162176A NO16217666A NO118710B NO 118710 B NO118710 B NO 118710B NO 162176 A NO162176 A NO 162176A NO 16217666 A NO16217666 A NO 16217666A NO 118710 B NO118710 B NO 118710B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- carbon atoms
- phenyl
- hydrogen
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- -1 chloroformic acid ester Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 20
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000001519 thymoleptic effect Effects 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 229960001826 dimethylphthalate Drugs 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
- URPOKCTXTOAWMI-UHFFFAOYSA-N 3,3-dimethyl-1h-2-benzofuran Chemical compound C1=CC=C2C(C)(C)OCC2=C1 URPOKCTXTOAWMI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 150000002642 lithium compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001671 psychotherapy Methods 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- JLRUQEPMSDFFSL-UHFFFAOYSA-N 1-phenyl-3,4-dihydro-1h-isochromene Chemical compound O1CCC2=CC=CC=C2C1C1=CC=CC=C1 JLRUQEPMSDFFSL-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 description 1
- QLHYVFSGYNVMPW-UHFFFAOYSA-N 3-chloro-n-methylpropan-1-amine Chemical compound CNCCCCl QLHYVFSGYNVMPW-UHFFFAOYSA-N 0.000 description 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000000891 anti-reserpine Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 201000003104 endogenous depression Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 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
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- RIZSFFYMJKBPTO-UHFFFAOYSA-N n,n-dimethyl-3-(1-phenyl-3,4-dihydroisochromen-1-yl)propan-1-amine Chemical compound O1CCC2=CC=CC=C2C1(CCCN(C)C)C1=CC=CC=C1 RIZSFFYMJKBPTO-UHFFFAOYSA-N 0.000 description 1
- ANLMKUQEPXRMGV-UHFFFAOYSA-N n-butyl-n-(3-chloropropyl)butan-1-amine Chemical compound CCCCN(CCCC)CCCCl ANLMKUQEPXRMGV-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 229960001158 nortriptyline Drugs 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- 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
- C07D311/76—Benzo[c]pyrans
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/18—Diazo-type processes, e.g. thermal development, or agents therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Lift Valve (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44075265A | 1965-03-18 | 1965-03-18 | |
| GB1185565A GB1102762A (en) | 1965-03-19 | 1965-03-19 | Phthalane, isochromane and isochromene derivatives |
| US75950368A | 1968-09-12 | 1968-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118710B true NO118710B (en:Method) | 1970-02-02 |
Family
ID=27256742
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO162148A NO123675B (en:Method) | 1965-03-18 | 1966-03-17 | |
| NO162175A NO118709B (en:Method) | 1965-03-18 | 1966-03-18 | |
| NO162176A NO118710B (en:Method) | 1965-03-18 | 1966-03-18 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO162148A NO123675B (en:Method) | 1965-03-18 | 1966-03-17 | |
| NO162175A NO118709B (en:Method) | 1965-03-18 | 1966-03-18 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US3446620A (en:Method) |
| BE (2) | BE677903A (en:Method) |
| BR (3) | BR6677980D0 (en:Method) |
| CH (2) | CH491102A (en:Method) |
| DE (3) | DE1543715C3 (en:Method) |
| DK (3) | DK114981B (en:Method) |
| FI (2) | FI48731C (en:Method) |
| FR (1) | FR5873M (en:Method) |
| GB (2) | GB1143702A (en:Method) |
| MY (2) | MY7300010A (en:Method) |
| NL (3) | NL6603604A (en:Method) |
| NO (3) | NO123675B (en:Method) |
| SE (3) | SE326194B (en:Method) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883551A (en) * | 1969-08-25 | 1975-05-13 | Little Inc A | Thienobenzopyrans and thiopyranobenzopyrans |
| US3670088A (en) * | 1969-10-14 | 1972-06-13 | Ayerst Mckenna & Harrison | Method of treating hyperchlorhydria and/or associated conditions |
| US3661590A (en) * | 1970-08-14 | 1972-05-09 | Addressograph Multigraph | Two component diazo-type developing process |
| US3880885A (en) * | 1971-11-23 | 1975-04-29 | Sandoz Ag | Tertiary aminoethyl isochromans and isocoumarins |
| US3934024A (en) * | 1971-12-20 | 1976-01-20 | Sharps Associates | Method of producing analgesia and compositions useful therein |
| US3987190A (en) * | 1971-12-20 | 1976-10-19 | Sharps Associates | Method of treating hypertension with, and compositions useful therein containing, a 4H-thieno[2,3-c][1]benzopyran or a 3H,5H-thiopyrano[2,3-c][1] |
| BE794081A (fr) * | 1972-01-27 | 1973-05-16 | Cortial | Nouveaux produits de reaction entre une amine primaire et un aldehyde |
| US4043816A (en) * | 1972-05-26 | 1977-08-23 | Oce-Van Der Grinten N.V. | Photographic process for making diazotype copies utilizing small quantity of liquid developer |
| NL172373C (nl) * | 1972-05-26 | 1983-08-16 | Oce Van Der Grinten Nv | Werkwijze voor het vervaardigen van diazotypkopieen. |
| JPS5119536A (en) * | 1974-08-09 | 1976-02-16 | Bunshodo Co Ltd | Jiazofukushaniokeru aminkeigenzoeki |
| NL176020C (nl) * | 1974-09-13 | 1985-02-01 | Oce Van Der Grinten Nv | Werkwijze voor het vervaardigen van diazotypkopieen, alsmede diazotypmateriaal voor het uitvoeren van deze werkwijze. |
| GB1484339A (en) * | 1974-11-20 | 1977-09-01 | Ozalid Group Holdings Ltd | Development of diazotype materials |
| DE2628094A1 (de) * | 1975-06-30 | 1977-01-27 | Ricoh Kk | Nassentwickler zum entwickeln von zweikomponenten-diazotypiematerialien |
| JPS5919549B2 (ja) * | 1976-01-01 | 1984-05-07 | 武田薬品工業株式会社 | 異節環状化合物 |
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| JPS5840743B2 (ja) * | 1976-10-04 | 1983-09-07 | 京セラミタ株式会社 | 湿式複写機の現像装置 |
| US4090879A (en) * | 1976-11-15 | 1978-05-23 | Gaf Corporation | Developing solutions for 2-component diazo-type materials |
| US4711960A (en) * | 1977-10-31 | 1987-12-08 | The Upjohn Company | Isochromans |
| US4250181A (en) * | 1977-10-31 | 1981-02-10 | The Upjohn Company | Methods of treating psychosis |
| US4487774A (en) * | 1977-10-31 | 1984-12-11 | The Upjohn Company | Isochromans |
| US4247553A (en) * | 1977-10-31 | 1981-01-27 | The Upjohn Company | Methods of treating psychosis |
| US4153612A (en) * | 1977-10-31 | 1979-05-08 | The Upjohn Company | 2-Benzoxepins |
| US4250175A (en) * | 1977-10-31 | 1981-02-10 | Mccall John M | Methods of treating psychosis |
| US4577021A (en) * | 1977-10-31 | 1986-03-18 | The Upjohn Company | 1H-2-Benzopyran-1-yl alkyl on 1-(isochroman-1-yl)alkyl piperazines |
| US4179510A (en) * | 1977-10-31 | 1979-12-18 | The Upjohn Company | Methods of treating psychosis |
| US4556656A (en) * | 1978-10-23 | 1985-12-03 | The Upjohn Company | 2-Benzoxepins |
| US4370406A (en) * | 1979-12-26 | 1983-01-25 | Richardson Graphics Company | Developers for photopolymer lithographic plates |
| US4343884A (en) * | 1980-12-29 | 1982-08-10 | Andrews Paper & Chemical Co., Inc. | Diazotype developing process and acidic developer with amine base salt |
| US4360532A (en) * | 1981-01-29 | 1982-11-23 | E. R. Squibb & Sons, Inc. | Substituted chromans |
| US4500543A (en) * | 1982-06-01 | 1985-02-19 | Abbott Laboratories | Substituted 1-aminomethyl-phthalans |
| US4649204A (en) * | 1983-05-23 | 1987-03-10 | Mcneilab, Inc. | Dialkanolamine derivatives |
| US4602035A (en) * | 1983-12-07 | 1986-07-22 | Hoechst-Roussel Pharmaceuticals Inc. | Antidepressant (3-aryl-2,3-dihydrobenzofuran-3-yl)alkylamines |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| DK0737189T3 (da) * | 1993-12-28 | 2000-03-06 | Upjohn Co | Heterocycliske forbindelser til behandling af CNS-forstyrrelser og cardiovaskulære forstyrrelser |
| US5752121A (en) * | 1995-09-27 | 1998-05-12 | Eastman Kodak Company | Photographic processing apparatus |
| TR200000066T2 (tr) | 1997-07-08 | 2000-11-21 | H. Lundbeck A/S | Sitalopram hazırlanması için yöntem. |
| UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| CN1286687A (zh) | 1997-11-11 | 2001-03-07 | H·隆德贝克有限公司 | 制备西酞普兰的方法 |
| HU228576B1 (en) | 1998-10-20 | 2013-04-29 | Lundbeck & Co As H | Method for the preparation of citalopram |
| AR021509A1 (es) * | 1998-12-08 | 2002-07-24 | Lundbeck & Co As H | Derivados de benzofurano, su preparacion y uso |
| EA003057B1 (ru) | 1998-12-23 | 2002-12-26 | Х.Лундбекк А/С | Способ получения 5-цианофталида |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| BR9917346A (pt) * | 1999-04-14 | 2002-02-26 | Lundbeck & Co As H | Método para preparação de citalopram intermadiário e utilização do mesmo |
| ITMI991581A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ITMI991579A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| AR021155A1 (es) * | 1999-07-08 | 2002-06-12 | Lundbeck & Co As H | Tratamiento de desordenes neuroticos |
| CH692298A5 (de) | 1999-10-25 | 2002-04-30 | Lundbeck & Co As H | Verfahren zur Herstellung von Zwischenstufen für die Citalopramsynthese sowie zur Herstellung von Escitalopram. |
| ATE277032T1 (de) | 1999-10-25 | 2004-10-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| DK1246812T3 (da) | 1999-12-28 | 2004-07-05 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
| PL198803B1 (pl) | 1999-12-30 | 2008-07-31 | Lundbeck & Co As H | Sposób wytwarzania 5-cyjano-3H-izobenzofuran-1-onu |
| SK286879B6 (sk) * | 2000-01-14 | 2009-07-06 | H. Lundbeck A/S | Spôsob prípravy 5-kyanoftalidu |
| FR2805812A1 (fr) | 2000-02-24 | 2001-09-07 | Lundbeck & Co As H | Procede de preparation du citalopram |
| NL1017417C1 (nl) | 2000-03-03 | 2001-03-16 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| PL357022A1 (en) * | 2000-03-13 | 2004-07-12 | H.Lundbeck A/S | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| GB2357762B (en) * | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| NZ521201A (en) * | 2000-03-13 | 2004-02-27 | H | Method for the preparation of citalopram |
| WO2001068630A1 (en) | 2000-03-14 | 2001-09-20 | H. Lundbeck A/S | Method for the preparation of citalopram |
| SK14812002A3 (sk) * | 2000-03-16 | 2003-02-04 | H. Lundbeck A/S | Spôsob prípravy 5-kyano-1-(4-fluórfenyl)-1,3-dihydrobenzofuránov a antidepresívny farmaceutický prostriedok |
| AR032455A1 (es) | 2000-05-12 | 2003-11-12 | Lundbeck & Co As H | Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva |
| CA2354880C (en) | 2000-08-18 | 2003-06-03 | H. Lundbeck A/S | Method for the preparation of citalopram |
| KR100439329B1 (ko) | 2000-12-22 | 2004-07-07 | 하. 룬트벡 아크티에 셀스카브 | 순수한 시탈로프람의 제조방법 |
| DK1181272T3 (da) * | 2000-12-28 | 2002-12-30 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af rent citalopram |
| JP2004527551A (ja) * | 2001-05-01 | 2004-09-09 | ハー・ルンドベック・アクチエゼルスカベット | エナンチオ純粋なエスシタロプラムの使用方法 |
| JP2005525993A (ja) * | 2001-07-31 | 2005-09-02 | ハー・ルンドベック・アクチエゼルスカベット | エスシタロプラムを含む結晶性組成物 |
| IN192863B (en:Method) * | 2001-11-13 | 2004-05-22 | Ranbaxy Lab Ltd | |
| CA2381341A1 (en) * | 2002-04-09 | 2003-10-09 | Torcan Chemical Ltd. | Process and intermediates for preparing escitalopram |
| AU2003237492A1 (en) * | 2002-06-10 | 2003-12-22 | Acadia Pharmaceuticals Inc. | Urotensin ii receptor modulators |
| US6812355B2 (en) | 2002-10-22 | 2004-11-02 | Sekhsaria Chemicals Limited | Process for the manufacture of citalopram hydrobromide from 5-bromophthalide |
| CN1751029A (zh) * | 2003-02-19 | 2006-03-22 | 阿卡蒂亚药品公司 | 2－氨乙基取代的嘧啶－2－酮、环丙烷、吡唑啉、嘧啶和苯并噻唑及其作为尿压素ⅱ和生长激素抑制素5 受体配体的应用 |
| US8022232B2 (en) * | 2007-09-11 | 2011-09-20 | H. Lundbeck A/S | Method for manufacture of escitalopram |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3103519A (en) * | 1963-09-10 | I-benzoxacycloalkanecarboxyoc acids | ||
| US3226402A (en) * | 1965-12-28 | And process of making and using same | ||
| GB256868A (en) * | 1926-02-10 | 1926-08-19 | Emil Gronau | Improvements in or relating to photographic processes and apparatus |
| NL27513C (en:Method) * | 1927-08-22 | |||
| US1757950A (en) * | 1927-10-26 | 1930-05-13 | Dietzgen Eugene Co | Developing apparatus |
| US1829583A (en) * | 1928-11-05 | 1931-10-27 | Carbide & Carbon Chem Corp | Process of removing finish coatings |
| US1795344A (en) * | 1929-01-11 | 1931-03-10 | Bruning Charles Co Inc | Paper-developing apparatus |
| DE528317C (de) * | 1929-12-19 | 1931-06-27 | Le Film Ozaphane Sa | Verfahren zum Entwickeln und Fixieren von kinematographischen Filmen aus einer wasserdurchlaessigen, in ihrer Masse sensibilisierten Schicht |
| US1796344A (en) * | 1930-05-12 | 1931-03-17 | Handy Things Mfg Company | Towel rack |
| FR741172A (en:Method) * | 1931-11-09 | 1933-02-08 | ||
| US2262428A (en) * | 1935-05-11 | 1941-11-11 | Shell Dev | Process for the treatment of oil or gas wells |
| NL53196C (nl) * | 1939-01-19 | 1940-11-15 | Chemische Fabriek | werkwijze en inrichting voor het ontwikkelen en/of fixeeren van lichtdrukken, in het bijzonder diazotypieen en blauwdrukken, volgens de zoogenaamde half-natte methode |
| DE736715C (de) * | 1939-02-17 | 1943-06-30 | Naamlooze Vennootschap Chemisc | Verfahren und Vorrichtung zum Entwickeln und/oder Fixieren von Lichtpausen nach dem Halbnass-Verfahren |
| US2308058A (en) * | 1940-10-03 | 1943-01-12 | Huey Co | Developer for diazo prints |
| DE889548C (de) * | 1942-02-19 | 1953-09-10 | Kalle & Co Ag | Verfahren zur Entwicklung von wasserabstossenden Diazo-Lichtpausschichten |
| US2551634A (en) * | 1945-12-17 | 1951-05-08 | Price Robert Hamilton | Liquid soap composition |
| BE502985A (en:Method) * | 1950-05-03 | |||
| US2820760A (en) * | 1952-08-13 | 1958-01-21 | Dick Co Ab | Fluid compositions for use in spirit duplication |
| US2981171A (en) * | 1958-03-06 | 1961-04-25 | Bruning Charles Co Inc | Developer process and apparatus |
| US3177149A (en) * | 1960-07-12 | 1965-04-06 | Whirlpool Co | Laundering composition |
| US3101349A (en) * | 1962-05-07 | 1963-08-20 | Searle & Co | Optionally 17-alkylated 17-oxygenated-2-oxaandrostanes and intermediates |
| US3203797A (en) * | 1962-10-16 | 1965-08-31 | Andrews Paper & Chem Co Inc | Thermal diazotype method and developer sheet for use therein |
| US3255007A (en) * | 1963-03-19 | 1966-06-07 | Keuffel & Esser Co | Diazotype reproduction materials |
| NL6411489A (en:Method) * | 1963-10-12 | 1965-04-13 | ||
| US3348947A (en) * | 1963-12-18 | 1967-10-24 | Ibm | Diazo print process |
| US3331690A (en) * | 1964-06-08 | 1967-07-18 | Ibm | Development of diazotype papers without a coupler |
-
0
- GB GB1143703D patent/GB1143703A/en active Active
- GB GB1143702D patent/GB1143702A/en active Active
-
1965
- 1965-03-18 US US440752A patent/US3446620A/en not_active Expired - Lifetime
-
1966
- 1966-03-03 US US540438A patent/US3467675A/en not_active Expired - Lifetime
- 1966-03-09 DE DE1543715A patent/DE1543715C3/de not_active Expired
- 1966-03-09 DE DE1543714A patent/DE1543714C3/de not_active Expired
- 1966-03-11 CH CH349366A patent/CH491102A/de not_active IP Right Cessation
- 1966-03-11 CH CH349866A patent/CH475232A/de not_active IP Right Cessation
- 1966-03-15 DK DK131166AA patent/DK114981B/da unknown
- 1966-03-15 DK DK130966AA patent/DK134415B/da unknown
- 1966-03-15 DK DK131266AA patent/DK112531B/da unknown
- 1966-03-16 BE BE677903D patent/BE677903A/xx not_active IP Right Cessation
- 1966-03-17 NO NO162148A patent/NO123675B/no unknown
- 1966-03-18 BR BR177980/66A patent/BR6677980D0/pt unknown
- 1966-03-18 SE SE03601/66A patent/SE326194B/xx unknown
- 1966-03-18 FI FI660706A patent/FI48731C/fi active
- 1966-03-18 DE DE1522449A patent/DE1522449C3/de not_active Expired
- 1966-03-18 NL NL6603604A patent/NL6603604A/xx unknown
- 1966-03-18 BR BR177982/66A patent/BR6677982D0/pt unknown
- 1966-03-18 SE SE03600/66A patent/SE326193B/xx unknown
- 1966-03-18 NO NO162175A patent/NO118709B/no unknown
- 1966-03-18 FI FI660705A patent/FI48730C/fi active
- 1966-03-18 NO NO162176A patent/NO118710B/no unknown
- 1966-03-18 NL NL6603603A patent/NL6603603A/xx unknown
- 1966-03-18 BE BE678035D patent/BE678035A/xx unknown
- 1966-03-18 NL NL6603606A patent/NL6603606A/xx unknown
- 1966-03-18 SE SE03652/66A patent/SE327141B/xx unknown
- 1966-03-18 BR BR177971/66A patent/BR6677971D0/pt unknown
- 1966-03-19 FR FR54185A patent/FR5873M/fr not_active Expired
-
1968
- 1968-09-12 US US759503A patent/US3578452A/en not_active Expired - Lifetime
-
1973
- 1973-12-31 MY MY197310A patent/MY7300010A/xx unknown
- 1973-12-31 MY MY19739A patent/MY7300009A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO118710B (en:Method) | ||
| NO162176B (no) | Middel for bekjempelse av plantesykdommer og anvendelse derav. | |
| Boekelheide et al. | Reissert Compounds. Further Alkylation Studies and a Novel Rearrangement1 | |
| US2684965A (en) | Aminoalkylpiperidines | |
| MXPA02006499A (es) | Derivados de fenilpiperazinilo. | |
| NO126734B (en:Method) | ||
| US3705907A (en) | 4-(2-hydroxy)-3-aminopropoxy)-indole derivatives | |
| NO860319L (no) | Fremgangsmaate for fremstillig av terapeutisk aktive 4h-1-benzopyran-4-on-derivater og deres svovelholdige analoger. | |
| NO125911B (en:Method) | ||
| SU772484A3 (ru) | Способ получени производных бензодиазепинона или их солей | |
| JPH02240053A (ja) | アミノアルコキシフェニル誘導体、その製法およびそれを含有する組成物 | |
| JPS584781A (ja) | テトラヒドロピリジン及びピペリジン誘導体の製法 | |
| CS207619B2 (en) | Method of making the new derivatives of 5,11-dihydro-6h-pyrido 2,3-b 1,4 benzodiazepin-6-on | |
| PL89037B1 (en:Method) | ||
| US2355659A (en) | Piperidine derivatives and process for the manufacture of the same | |
| NO126371B (en:Method) | ||
| GB2056435A (en) | Novel Tetrahydropyridine and Piperidine Substituted Benzofuranes and Related Compounds | |
| US3073826A (en) | 3-pyrrolidylmethyl-4-quinazolones | |
| US3523124A (en) | Antidepressant amino-alkyl-substituted phthalanes,compositions and method of treating | |
| NO162907B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive bis-(piperazinyl-resp. homopiperazinyl)-alkaner. | |
| CA1056834A (en) | 3-(4-bromophenyl)-n-methyl-3-(3-pyridyl)-allylamine | |
| US3040031A (en) | N-heterocyclic compounds | |
| US3075986A (en) | (1-piperdidylalkyl) derivatives of 3-indole | |
| NO124687B (en:Method) | ||
| NO843203L (no) | Fremgangsmaate for fremstilling av indolderivater |