NO119801B - - Google Patents

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Info

Publication number: NO119801B
Authority: NO; Norway
Prior art keywords: amino; radical; phenyl; trifluoromethylphenyl; ethyl
Prior art date: 1966-04-15

Application number

NO167741A

Other languages

English (en)

Norwegian (no)

Inventor

Douarec J Le

L Beregi

P Hugon

Original Assignee

Science Union & Cie

Priority date (The priority date 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 date listed.)

1966-04-15

Filing date

1967-04-14

Publication date

1970-07-06

1967-04-14 Application filed by Science Union & Cie filed Critical Science Union & Cie

1970-07-06 Publication of NO119801B publication Critical patent/NO119801B/no

Links

-1 hydroxyl- Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 9
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 5
208000022531 anorexia Diseases 0.000 claims description 4
206010061428 decreased appetite Diseases 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
239000011707 mineral Substances 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
LSPHULWDVZXLIL-LDWIPMOCSA-N (?)-Camphoric acid Chemical compound CC1(C)[C@@H](C(O)=O)CC[C@@]1(C)C(O)=O LSPHULWDVZXLIL-LDWIPMOCSA-N 0.000 claims description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000001294 propane Substances 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000155 melt Substances 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000000047 product Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical compound CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
230000036528 appetite Effects 0.000 description 2
235000019789 appetite Nutrition 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000012265 solid product Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
231100001274 therapeutic index Toxicity 0.000 description 2
WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
MLBHFBKZUPLWBD-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound CC(N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-UHFFFAOYSA-N 0.000 description 1
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
NOYKUYNVZHTPCI-UHFFFAOYSA-N 1-phenylcyclopentane-1-carbonyl chloride Chemical compound C=1C=CC=CC=1C1(C(=O)Cl)CCCC1 NOYKUYNVZHTPCI-UHFFFAOYSA-N 0.000 description 1
VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-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
CUSDKBHKWFSTTH-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]acetyl chloride Chemical compound CC(C)CC1=CC=C(CC(Cl)=O)C=C1 CUSDKBHKWFSTTH-UHFFFAOYSA-N 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
DVIHKVWYFXLBEM-UHFFFAOYSA-N 2-hydroxybenzoyl chloride Chemical compound OC1=CC=CC=C1C(Cl)=O DVIHKVWYFXLBEM-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
QGXMHCMPIAYMGT-UHFFFAOYSA-N 2-phenylbutanoyl chloride Chemical compound CCC(C(Cl)=O)C1=CC=CC=C1 QGXMHCMPIAYMGT-UHFFFAOYSA-N 0.000 description 1
FOTITZRWZUAVPH-UHFFFAOYSA-N 2-phenylpropanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC=C1 FOTITZRWZUAVPH-UHFFFAOYSA-N 0.000 description 1
RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
CPYJFDPRIHGAKB-UHFFFAOYSA-N N-propan-2-yl-N-(trifluoromethyl)aniline Chemical compound CC(C)N(C(F)(F)F)C1=CC=CC=C1 CPYJFDPRIHGAKB-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
CJAVTWRYCDNHSM-UHFFFAOYSA-N benzoic acid 2-[1-[3-(trifluoromethyl)phenyl]propan-2-ylamino]ethyl ester Chemical compound C=1C=CC=CC=1C(=O)OCCNC(C)CC1=CC=CC(C(F)(F)F)=C1 CJAVTWRYCDNHSM-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000012230 colorless oil Substances 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
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-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
150000003254 radicals Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton

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)

NO167741A 1966-04-15 1967-04-14 NO119801B (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB06660/66A GB1175516A (en)	1966-04-15	1966-04-15	New Phenyl-Aminopropane Derivatives and Preparations Containing them

Publications (1)

Publication Number	Publication Date
NO119801B true NO119801B (fi)	1970-07-06

Family

ID=10081320

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO167741A NO119801B (fi)	1966-04-15	1967-04-14

Country Status (14)

Country	Link
US (1)	US3607909A (fi)
AT (1)	AT273918B (fi)
BE (1)	BE696851A (fi)
CH (1)	CH490330A (fi)
DK (1)	DK123351B (fi)
ES (1)	ES339391A1 (fi)
FI (1)	FI46373C (fi)
FR (2)	FR1517587A (fi)
GB (1)	GB1175516A (fi)
GR (1)	GR32755B (fi)
NL (1)	NL6705198A (fi)
NO (1)	NO119801B (fi)
OA (1)	OA02581A (fi)
SE (1)	SE327417B (fi)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3700680A (en) *	1967-10-13	1972-10-24	Dainippon Pharmaceutical Co	Aminoalkanol esters and their pharmaceutically acceptable acid-addition salts
US4237165A (en) *	1976-06-04	1980-12-02	Science Union Et Cie	Treatment of carbohydrate metabolism disorders
IT1089009B (it) *	1977-10-28	1985-06-10	Btb Ind Chimica	Processo per la preparazione dell'1-(3-trifluorometilfenil)-2-(2-benzoilossietilammino)-propano
FR2502952A1 (fr) *	1981-04-07	1982-10-08	Science Union & Cie	Nouveau medicament a base de chlorhydrate de benfluorex pour le traitement du diabete
FR2684101B1 (fr) *	1991-11-22	1993-12-31	Adir Cie	Nouveaux derives de benzoate d'ethanolamine, leur procede de preparation et les compositions pharmaceutiques les renfermant.
DK0863981T3 (da) *	1996-08-01	2010-02-01	Dale Wallis	Detektering, forebyggelse og behandling af papillomatous digital dermatitis
US6083497A (en) *	1997-11-05	2000-07-04	Geltex Pharmaceuticals, Inc.	Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers
ITMI20012597A1 (it) *	2001-12-11	2003-06-11	Synteco Spa	Sintesi dell'1-(3-trifluorometilfenil)-2-(-2-benzoilossietilammino)-propano
CN100400503C (zh) *	2006-09-21	2008-07-09	上海大学	5，5，5-三氟-4-(4-甲氧基苯基氨基)戊酸甲酯及其合成方法
US8100429B2 (en)	2008-03-31	2012-01-24	Artsana Usa, Inc.	Three dimensional folding stroller with infant carrier attachment and one hand actuated seat recline
CN101880238B (zh) *	2010-07-06	2014-05-21	沈阳药科大学	苯甲酸-2-({1-甲基-2-[3-(三氟甲基)-苯基]乙基}氨基)乙酯盐酸盐的制备方法
PE20211065A1 (es)	2018-07-27	2021-06-09	Xenon Pharmaceuticals Inc	Metodo para tratar la epilepsia

1966
- 1966-04-15 GB GB06660/66A patent/GB1175516A/en not_active Expired
1967
- 1967-03-22 SE SE04095/67A patent/SE327417B/xx unknown
- 1967-03-23 GR GR670132755A patent/GR32755B/el unknown
- 1967-03-28 OA OA52836A patent/OA02581A/xx unknown
- 1967-03-31 US US627323A patent/US3607909A/en not_active Expired - Lifetime
- 1967-04-05 FR FR101584A patent/FR1517587A/fr not_active Expired
- 1967-04-10 FI FI671050A patent/FI46373C/fi active
- 1967-04-10 BE BE696851D patent/BE696851A/xx not_active IP Right Cessation
- 1967-04-10 AT AT337367A patent/AT273918B/de active
- 1967-04-13 NL NL6705198A patent/NL6705198A/xx unknown
- 1967-04-14 CH CH530667A patent/CH490330A/fr not_active IP Right Cessation
- 1967-04-14 DK DK205767AA patent/DK123351B/da not_active IP Right Cessation
- 1967-04-14 NO NO167741A patent/NO119801B/no unknown
- 1967-04-15 ES ES339391A patent/ES339391A1/es not_active Expired
1968
- 1968-12-23 FR FR112833A patent/FR6564M/fr not_active Expired

Also Published As

Publication number	Publication date
ES339391A1 (es)	1968-10-01
BE696851A (fi)	1967-10-10
GR32755B (el)	1967-08-29
DK123351B (da)	1972-06-12
DE1593991B2 (de)	1973-02-01
FI46373C (fi)	1973-03-12
CH490330A (fr)	1970-05-15
DE1593991A1 (de)	1972-03-16
FI46373B (fi)	1972-11-30
SE327417B (fi)	1970-08-24
FR6564M (fi)	1968-12-23
NL6705198A (fi)	1967-10-16
US3607909A (en)	1971-09-21
OA02581A (fr)	1970-05-05
GB1175516A (en)	1969-12-23
FR1517587A (fr)	1968-03-15
AT273918B (de)	1969-08-25

Publication	Publication Date	Title
US4814352A (en)	1989-03-21	Therapeutic agents
NO153082B (no)	1985-10-07	Apparat for stapping av en rynket roerformet omhylling
KR100523366B1 (ko)	2005-10-20	티에닐아졸일알콕시에탄아민, 이의 제조방법 및 이의 용도
NO119801B (fi)	1970-07-06
US4254274A (en)	1981-03-03	Cycloalkylidenemethylphenylacetic acid derivatives and process for the preparation thereof
JPS63146874A (ja)	1988-06-18	インドール誘導体
NO314581B1 (no)	2003-04-14	Opplösning av aminer
US3383411A (en)	1968-05-14	4-alkanoylphenoxy-alkanoic acids
DK152670B (da)	1988-04-11	Analogifremgangsmaade til fremstilling af 1-(4-aryl-4-cyano-cyclohexyl)-4-aryl-4-piperidincarboxylsyre-derivater eller farmaceutisk acceptable syreadditionssalte og stereokemiske isomere deraf
CZ180898A3 (cs)	1999-05-12	Způsob a meziprodukty pro výrobu 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidinu
AU644296B2 (en)	1993-12-02	2-(1-piperidyl)ethanol derivatives, their preparation and their therapeutic application
CA1086742A (en)	1980-09-30	Preparation of 1-substituted-4-aroyl-4-hydroxy and -4- acyloxypiperidines
IE49339B1 (en)	1985-09-18	New 3h-naphth(1,2-d)imidazoles,processes for preparing them,compounds for use as antiinflammatory and antimicrobial agents and compositions for that use containing them
US4010202A (en)	1977-03-01	5,6-Dihydroxy aminotetralol compounds
NO163814B (no)	1990-04-17	Analogifremgangsmaate for fremstilling av terapeutisk aktive 1-substituerte 4-hydroksymetyl-pyrrolidinon-derivater.
US4515944A (en)	1985-05-07	1,5-Diphenyl-2-haloalkylpyrazolin-3-one intermediates
IL25953A (en)	1970-10-30	Phenanthridine derivatives and process for the manufacture thereof
US4339576A (en)	1982-07-13	Anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory 1-[(benzoylphenyl)-lower-alkyl]piperidines and analogs thereof
NO150041B (no)	1984-04-30	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive lactamforbindelser
US3775479A (en)	1973-11-27	Amine compounds
US4076821A (en)	1978-02-28	4,4-Diphenylcycloalkylpiperidines and psychotropic compositions thereof
EP0052311A1 (en)	1982-05-26	1-((Benzoylphenyl) - lower-alkyl) piperidines and carbinol analogs and preparation thereof
JPH069402A (ja)	1994-01-18	抗潰瘍剤
US2485662A (en)	1949-10-25	Alpha-(aminoalkyl)-stilbenes
JPH09504014A (ja)	1997-04-22	カルシウムチャネル拮抗薬としてのアミン誘導体類