NO133198B - - Google Patents
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- Publication number
- NO133198B NO133198B NO3825/71A NO382571A NO133198B NO 133198 B NO133198 B NO 133198B NO 3825/71 A NO3825/71 A NO 3825/71A NO 382571 A NO382571 A NO 382571A NO 133198 B NO133198 B NO 133198B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- approx
- filtered
- product
- preparations
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 206010010904 Convulsion Diseases 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RWZSFUHBNNZPJU-UHFFFAOYSA-N 2-(2-aminophenyl)-n-methylacetamide Chemical group CNC(=O)CC1=CC=CC=C1N RWZSFUHBNNZPJU-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FAGCGLVYZVONBW-UHFFFAOYSA-N 2-(2-aminophenyl)-n-ethylacetamide Chemical compound CCNC(=O)CC1=CC=CC=C1N FAGCGLVYZVONBW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003929 acidic solution Substances 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
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 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
- WMUZDBZPDLHUMW-UHFFFAOYSA-N (2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1[N+]([O-])=O WMUZDBZPDLHUMW-UHFFFAOYSA-N 0.000 description 2
- VGAVDFWIHUETOY-UHFFFAOYSA-N 2-(2-amino-4-chlorophenyl)-n-methylacetamide Chemical compound CNC(=O)CC1=CC=C(Cl)C=C1N VGAVDFWIHUETOY-UHFFFAOYSA-N 0.000 description 2
- FLZUSUKBKOZJLG-UHFFFAOYSA-N 2-(4-chloro-2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1[N+]([O-])=O FLZUSUKBKOZJLG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 230000001914 calming effect Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 208000028329 epileptic seizure Diseases 0.000 description 2
- 206010022437 insomnia Diseases 0.000 description 2
- ONHWNARPSWLBLK-UHFFFAOYSA-N n-methyl-2-(2-nitrophenyl)acetamide Chemical compound CNC(=O)CC1=CC=CC=C1[N+]([O-])=O ONHWNARPSWLBLK-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- XODRHOWZEUKZFD-UHFFFAOYSA-N 2-(2-aminophenyl)-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CC1=CC=CC=C1N XODRHOWZEUKZFD-UHFFFAOYSA-N 0.000 description 1
- JBQZJVJEAYXBAT-UHFFFAOYSA-N 2-(2-aminophenyl)-n-propylacetamide Chemical compound CCCNC(=O)CC1=CC=CC=C1N JBQZJVJEAYXBAT-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- 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 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- AUPLPHUNRCIGDR-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC(=C1)Cl)CC(=O)NC Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)Cl)CC(=O)NC AUPLPHUNRCIGDR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YYWFADAFBVXZNR-UHFFFAOYSA-N n-ethyl-2-(2-nitrophenyl)acetamide Chemical compound CCNC(=O)CC1=CC=CC=C1[N+]([O-])=O YYWFADAFBVXZNR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4928270 | 1970-10-16 | ||
| GB3848371 | 1971-08-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133198B true NO133198B (de) | 1975-12-15 |
| NO133198C NO133198C (de) | 1976-03-24 |
Family
ID=26263823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3825/71A NO133198C (de) | 1970-10-16 | 1971-10-15 |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT310757B (de) |
| BE (1) | BE774033A (de) |
| CA (1) | CA969953A (de) |
| CH (1) | CH573410A5 (de) |
| DE (1) | DE2151487A1 (de) |
| DK (1) | DK131149B (de) |
| ES (1) | ES396073A1 (de) |
| FR (1) | FR2111670A1 (de) |
| HU (1) | HU162813B (de) |
| IE (1) | IE35662B1 (de) |
| IL (1) | IL37839A (de) |
| NL (1) | NL7114259A (de) |
| NO (1) | NO133198C (de) |
| SU (1) | SU493969A3 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1474399A (en) * | 1974-08-19 | 1977-05-25 | Ici Ltd | Cinnolin-3-yl carboxylic acids and derivatives thereof |
| GB1472766A (en) * | 1974-11-07 | 1977-05-04 | Ici Ltd | Hydroxycinnoline derivatives processes for their preparation and their use in pharmaceutical compositions |
| US4379929A (en) | 1981-03-19 | 1983-04-12 | Eli Lilly And Company | 4(1H)-Oxocinnoline-3-carboxylic acid derivatives |
| US4756740A (en) * | 1983-09-14 | 1988-07-12 | Lafarge Coppee | Pollen suppressant comprising a fused pyridazine |
| US7700595B2 (en) | 2005-03-01 | 2010-04-20 | Wyeth Llc | Cinnoline compounds |
-
1971
- 1971-09-24 IE IE1194/71A patent/IE35662B1/xx unknown
- 1971-09-28 CA CA123,923A patent/CA969953A/en not_active Expired
- 1971-10-05 DK DK484171AA patent/DK131149B/da unknown
- 1971-10-05 IL IL37839A patent/IL37839A/en unknown
- 1971-10-14 CH CH1500071A patent/CH573410A5/xx not_active IP Right Cessation
- 1971-10-15 NL NL7114259A patent/NL7114259A/xx unknown
- 1971-10-15 NO NO3825/71A patent/NO133198C/no unknown
- 1971-10-15 FR FR7137218A patent/FR2111670A1/fr active Granted
- 1971-10-15 BE BE774033A patent/BE774033A/xx unknown
- 1971-10-15 DE DE19712151487 patent/DE2151487A1/de active Pending
- 1971-10-16 ES ES396073A patent/ES396073A1/es not_active Expired
- 1971-10-16 HU HUIE480A patent/HU162813B/hu unknown
- 1971-10-18 AT AT942572A patent/AT310757B/de not_active IP Right Cessation
-
1973
- 1973-02-06 SU SU731880093A patent/SU493969A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| DK131149C (de) | 1975-11-10 |
| SU493969A3 (ru) | 1975-11-28 |
| IE35662L (en) | 1972-04-16 |
| IL37839A0 (en) | 1971-12-29 |
| NO133198C (de) | 1976-03-24 |
| CH573410A5 (de) | 1976-03-15 |
| AU3454871A (en) | 1973-04-19 |
| FR2111670A1 (en) | 1972-06-09 |
| IE35662B1 (en) | 1976-04-14 |
| BE774033A (fr) | 1972-04-17 |
| ES396073A1 (es) | 1974-10-16 |
| NL7114259A (de) | 1972-04-18 |
| CA969953A (en) | 1975-06-24 |
| IL37839A (en) | 1974-12-31 |
| HU162813B (de) | 1973-04-28 |
| FR2111670B1 (de) | 1975-10-10 |
| DK131149B (da) | 1975-06-02 |
| DE2151487A1 (de) | 1972-04-20 |
| AT310757B (de) | 1973-10-10 |
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