NO790648L - Fremgangsmaate for fremstilling av cykloalkyl-alkylbenzamider - Google Patents
Fremgangsmaate for fremstilling av cykloalkyl-alkylbenzamiderInfo
- Publication number
- NO790648L NO790648L NO790648A NO790648A NO790648L NO 790648 L NO790648 L NO 790648L NO 790648 A NO790648 A NO 790648A NO 790648 A NO790648 A NO 790648A NO 790648 L NO790648 L NO 790648L
- Authority
- NO
- Norway
- Prior art keywords
- mol
- methoxy
- acetone
- formula
- benzoic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- -1 2-methoxy-5-substituted benzoic acid Chemical class 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- QFIYFROFRTUSPW-UHFFFAOYSA-N [1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1CC1 QFIYFROFRTUSPW-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IUTPSVNWIWQIDX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)pyrazol-4-yl]ethanone Chemical compound C1=C(C(=O)C)C=NN1C1=CC=C(Cl)C=C1 IUTPSVNWIWQIDX-UHFFFAOYSA-N 0.000 description 2
- NAKZCKOHULJEID-UHFFFAOYSA-N 2-methoxy-5-(trifluoromethyl)benzoic acid Chemical compound COC1=CC=C(C(F)(F)F)C=C1C(O)=O NAKZCKOHULJEID-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000008346 aqueous phase Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-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
- VOQPCMLSRLWUEQ-UHFFFAOYSA-N 2-methoxy-3-(trifluoromethyl)benzoyl chloride Chemical compound COC1=C(C(Cl)=O)C=CC=C1C(F)(F)F VOQPCMLSRLWUEQ-UHFFFAOYSA-N 0.000 description 1
- KZZUPJSYJCNYMW-UHFFFAOYSA-N 2-methoxy-5-methylbenzenecarbothioyl chloride Chemical compound COC1=CC=C(C)C=C1C(Cl)=S KZZUPJSYJCNYMW-UHFFFAOYSA-N 0.000 description 1
- MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical class COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 description 1
- OUBZCDOQEMLMAB-UHFFFAOYSA-N 5-chlorosulfonyl-2-methoxybenzoic acid Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1C(O)=O OUBZCDOQEMLMAB-UHFFFAOYSA-N 0.000 description 1
- WBRILLISQMMNMD-UHFFFAOYSA-N 5-ethyl-2-methoxybenzenecarbothioyl chloride Chemical compound COC1=C(C(=S)Cl)C=C(C=C1)CC WBRILLISQMMNMD-UHFFFAOYSA-N 0.000 description 1
- BOLLTSUCKRNILK-UHFFFAOYSA-N COC1=C(C(=S)O)C=C(C=C1)CC Chemical compound COC1=C(C(=S)O)C=C(C=C1)CC BOLLTSUCKRNILK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- BZKGHSWMKGRQMK-UHFFFAOYSA-N N-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-(trifluoromethyl)benzamide Chemical compound C1(CC1)CN1C(CCC1)CNC(C1=C(C=CC(=C1)C(F)(F)F)OC)=O BZKGHSWMKGRQMK-UHFFFAOYSA-N 0.000 description 1
- 208000012545 Psychophysiologic disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AQZWYQHLYWDFEO-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-methylbenzenecarbothioamide Chemical compound COC1=CC=C(C)C=C1C(=S)NCC1N(CC2CC2)CCC1 AQZWYQHLYWDFEO-UHFFFAOYSA-N 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7805580A FR2418226A1 (fr) | 1978-02-27 | 1978-02-27 | Methoxy-2 alkylthio-5 benzamides et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO790648L true NO790648L (no) | 1979-08-28 |
Family
ID=9205110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO790648A NO790648L (no) | 1978-02-27 | 1979-02-26 | Fremgangsmaate for fremstilling av cykloalkyl-alkylbenzamider |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS54122269A (da) |
| AT (1) | AT373581B (da) |
| AU (1) | AU521854B2 (da) |
| BE (1) | BE874490A (da) |
| CA (1) | CA1105937A (da) |
| CH (1) | CH637378A5 (da) |
| DE (1) | DE2907377A1 (da) |
| DK (1) | DK82379A (da) |
| ES (1) | ES478073A1 (da) |
| FI (1) | FI790658A7 (da) |
| FR (1) | FR2418226A1 (da) |
| GB (1) | GB2014995B (da) |
| GR (1) | GR66973B (da) |
| IE (1) | IE47897B1 (da) |
| IL (1) | IL56747A0 (da) |
| IT (1) | IT1114210B (da) |
| LU (1) | LU80976A1 (da) |
| NL (1) | NL7901472A (da) |
| NO (1) | NO790648L (da) |
| NZ (1) | NZ189771A (da) |
| PT (1) | PT69290A (da) |
| SE (1) | SE430501B (da) |
| ZA (1) | ZA799808B (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT50889A (en) * | 1987-05-25 | 1990-03-28 | Foreshore Protection Pty Ltd | Anti-erosion cover |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2245628B1 (da) * | 1973-09-28 | 1977-03-11 | Ile De France |
-
1978
- 1978-02-27 FR FR7805580A patent/FR2418226A1/fr active Granted
-
1979
- 1979-02-26 NO NO790648A patent/NO790648L/no unknown
- 1979-02-26 SE SE7901708A patent/SE430501B/sv unknown
- 1979-02-26 CA CA322,283A patent/CA1105937A/en not_active Expired
- 1979-02-26 DE DE19792907377 patent/DE2907377A1/de not_active Withdrawn
- 1979-02-26 NZ NZ189771A patent/NZ189771A/xx unknown
- 1979-02-26 CH CH188379A patent/CH637378A5/fr not_active IP Right Cessation
- 1979-02-26 DK DK82379A patent/DK82379A/da not_active Application Discontinuation
- 1979-02-26 AU AU44604/79A patent/AU521854B2/en not_active Ceased
- 1979-02-26 IT IT20542/79A patent/IT1114210B/it active
- 1979-02-26 JP JP2247679A patent/JPS54122269A/ja active Pending
- 1979-02-26 NL NL7901472A patent/NL7901472A/xx not_active Application Discontinuation
- 1979-02-26 PT PT69290A patent/PT69290A/pt unknown
- 1979-02-26 ZA ZA00799808A patent/ZA799808B/xx unknown
- 1979-02-26 ES ES478073A patent/ES478073A1/es not_active Expired
- 1979-02-27 FI FI790658A patent/FI790658A7/fi not_active Application Discontinuation
- 1979-02-27 BE BE0/193730A patent/BE874490A/xx not_active IP Right Cessation
- 1979-02-27 AT AT0149479A patent/AT373581B/de not_active IP Right Cessation
- 1979-02-27 LU LU80976A patent/LU80976A1/fr unknown
- 1979-02-27 GB GB7906954A patent/GB2014995B/en not_active Expired
- 1979-02-27 IL IL56747A patent/IL56747A0/xx unknown
- 1979-02-27 GR GR58492A patent/GR66973B/el unknown
- 1979-08-08 IE IE558/79A patent/IE47897B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU521854B2 (en) | 1982-05-06 |
| GB2014995B (en) | 1982-07-28 |
| IE47897B1 (en) | 1984-07-11 |
| JPS54122269A (en) | 1979-09-21 |
| GR66973B (da) | 1981-05-15 |
| IE790558L (en) | 1979-08-27 |
| LU80976A1 (fr) | 1980-09-24 |
| ZA799808B (en) | 1980-06-25 |
| AU4460479A (en) | 1979-09-06 |
| CH637378A5 (fr) | 1983-07-29 |
| SE7901708L (sv) | 1979-08-28 |
| SE430501B (sv) | 1983-11-21 |
| CA1105937A (en) | 1981-07-28 |
| IT1114210B (it) | 1986-01-27 |
| NL7901472A (nl) | 1979-08-29 |
| IT7920542A0 (it) | 1979-02-26 |
| BE874490A (fr) | 1979-08-27 |
| FI790658A7 (fi) | 1979-08-28 |
| ATA149479A (de) | 1983-06-15 |
| FR2418226A1 (fr) | 1979-09-21 |
| IL56747A0 (en) | 1979-05-31 |
| FR2418226B1 (da) | 1980-11-07 |
| DE2907377A1 (de) | 1979-09-06 |
| PT69290A (fr) | 1979-03-01 |
| AT373581B (de) | 1984-02-10 |
| ES478073A1 (es) | 1979-05-16 |
| NZ189771A (en) | 1980-11-14 |
| GB2014995A (en) | 1979-09-05 |
| DK82379A (da) | 1979-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU820659A3 (ru) | Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/ | |
| DE3004370C2 (da) | ||
| NO164476B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk virksomme 1,2,3,5-tetrahydroimidazo-(2,1-b)-kinazoliner. | |
| SU1597096A3 (ru) | Способ получени производных дифенилпропиламина или их фармакологически приемлемых солей | |
| DE2909754A1 (de) | Neue benzofuran- und benzothiophenderivate, deren herstellung und deren verwendung als arzneimittel | |
| EP0074768A2 (en) | Alkanoylanilides | |
| DE69315085T2 (de) | 1,4-disubstituierte piperazine zur behandlung von asthma und entzündungen der atemwege | |
| DE68908425T2 (de) | Diharnstoffderivate, verwendbar als Medikamente, und Verfahren zu deren Herstellung. | |
| NO153001B (no) | Drivanordning for skip | |
| EP0496238A1 (de) | Substituierte Benzoxazepine und Benzthiazepine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln | |
| NO773300L (no) | Fremgangsmaate for fremstilling av nye eddiksyrederivater | |
| US4234742A (en) | Bis-(aryloxycarboxylic acid) compounds | |
| SU578884A3 (ru) | Способ получени производных триазолоизоиндола | |
| KR910005850B1 (ko) | 이미다조[1,5-a]피리미딘 유도체의 제조방법 | |
| DE3925496C2 (da) | ||
| US3257420A (en) | Carboxylic acids alpha-substituted by at least one cyclic radical | |
| NO790648L (no) | Fremgangsmaate for fremstilling av cykloalkyl-alkylbenzamider | |
| Cardani et al. | Synthesis of enantiomeric pure intermediate for the lactone portion of compactin and mevinolin | |
| CH622777A5 (da) | ||
| DD268940A5 (de) | Verfahren zur herstellung von neuen 3-(hydroxymethyl)-isochinolin-derivaten | |
| US5091403A (en) | Sulfinyl imidazole derivatives and antiulcer agents containing the same | |
| NO140010B (no) | Analogifremgangsmaate til fremstilling av terapeutisk virksomme 6-substituerte 3-karbetoksyhydrazinopyridaziner | |
| US4294838A (en) | Certain heterocyclic sulfoximide derivatives | |
| US4017623A (en) | Esters of 2-[(4-quinolyl)amino]-benzoic acids in analgesic and anti-inflammatory compositions | |
| US3598861A (en) | 2-(5'-phenyl-m-terphenyl - 4 - yloxy) lower aliphatic monocarbocyclic acids and esters thereof |