NO133803B - - Google Patents
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- Publication number
- NO133803B NO133803B NO4358/69A NO435869A NO133803B NO 133803 B NO133803 B NO 133803B NO 4358/69 A NO4358/69 A NO 4358/69A NO 435869 A NO435869 A NO 435869A NO 133803 B NO133803 B NO 133803B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- cyano
- therapeutically active
- phenylpropyl
- compounds
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000002496 gastric effect Effects 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 206010012735 Diarrhoea Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000001142 anti-diarrhea Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 2,2-di-phenyl-substituted butyronitrile compounds Chemical class 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- UFIVBRCCIRTJTN-UHFFFAOYSA-N difenoxin Chemical compound C1CC(C(=O)O)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 UFIVBRCCIRTJTN-UHFFFAOYSA-N 0.000 description 1
- VMIZTXDGZPTKIK-UHFFFAOYSA-N difenoxin hydrochloride Chemical compound [Cl-].C1CC(C(=O)O)(C=2C=CC=CC=2)CC[NH+]1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 VMIZTXDGZPTKIK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical class OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 208000026775 severe diarrhea Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77332468A | 1968-11-04 | 1968-11-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133803B true NO133803B (pl) | 1976-03-22 |
| NO133803C NO133803C (pl) | 1976-07-07 |
Family
ID=25097879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4358/69A NO133803C (pl) | 1968-11-04 | 1969-11-03 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3646207A (pl) |
| AT (1) | AT293387B (pl) |
| BE (1) | BE741155A (pl) |
| BR (1) | BR6913868D0 (pl) |
| CH (1) | CH517742A (pl) |
| CS (1) | CS156461B2 (pl) |
| DK (1) | DK129124B (pl) |
| ES (1) | ES373101A1 (pl) |
| FR (1) | FR2022531B1 (pl) |
| GB (1) | GB1234359A (pl) |
| IE (1) | IE33602B1 (pl) |
| IL (1) | IL33167A (pl) |
| LU (1) | LU59733A1 (pl) |
| NL (1) | NL146380B (pl) |
| NO (1) | NO133803C (pl) |
| PL (1) | PL80327B1 (pl) |
| RO (1) | RO57886A (pl) |
| SE (1) | SE354067B (pl) |
| SU (1) | SU489324A3 (pl) |
| YU (1) | YU34188B (pl) |
| ZA (1) | ZA697742B (pl) |
-
1968
- 1968-11-04 US US773324A patent/US3646207A/en not_active Expired - Lifetime
-
1969
- 1969-10-12 IL IL33167A patent/IL33167A/xx unknown
- 1969-10-17 IE IE1427/69A patent/IE33602B1/xx unknown
- 1969-10-28 CH CH1606069A patent/CH517742A/fr not_active IP Right Cessation
- 1969-10-31 LU LU59733D patent/LU59733A1/xx unknown
- 1969-10-31 SU SU1373679A patent/SU489324A3/ru active
- 1969-10-31 ES ES373101A patent/ES373101A1/es not_active Expired
- 1969-10-31 GB GB1234359D patent/GB1234359A/en not_active Expired
- 1969-11-03 PL PL1969136662A patent/PL80327B1/pl unknown
- 1969-11-03 YU YU2737/69A patent/YU34188B/xx unknown
- 1969-11-03 NO NO4358/69A patent/NO133803C/no unknown
- 1969-11-03 FR FR696937762A patent/FR2022531B1/fr not_active Expired
- 1969-11-03 SE SE15022/69A patent/SE354067B/xx unknown
- 1969-11-03 BR BR213868/69A patent/BR6913868D0/pt unknown
- 1969-11-03 BE BE741155D patent/BE741155A/xx unknown
- 1969-11-04 RO RO61465A patent/RO57886A/ro unknown
- 1969-11-04 CS CS727969A patent/CS156461B2/cs unknown
- 1969-11-04 ZA ZA697742A patent/ZA697742B/xx unknown
- 1969-11-04 DK DK580369AA patent/DK129124B/da not_active IP Right Cessation
- 1969-11-04 NL NL696916611A patent/NL146380B/xx not_active IP Right Cessation
- 1969-11-04 AT AT1034769A patent/AT293387B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| IL33167A0 (en) | 1969-12-31 |
| YU34188B (en) | 1979-02-28 |
| DE1953342B2 (de) | 1976-02-26 |
| NL146380B (nl) | 1975-07-15 |
| NO133803C (pl) | 1976-07-07 |
| ZA697742B (en) | 1971-06-30 |
| DE1953342A1 (de) | 1970-06-11 |
| ES373101A1 (es) | 1972-03-16 |
| PL80327B1 (pl) | 1975-08-30 |
| CH517742A (fr) | 1972-01-15 |
| IL33167A (en) | 1972-11-28 |
| AT293387B (de) | 1971-10-11 |
| BE741155A (pl) | 1970-05-04 |
| IE33602L (en) | 1970-05-04 |
| SE354067B (pl) | 1973-02-26 |
| GB1234359A (pl) | 1971-06-03 |
| LU59733A1 (pl) | 1970-01-12 |
| FR2022531A1 (pl) | 1970-07-31 |
| CS156461B2 (pl) | 1974-07-24 |
| NL6916611A (pl) | 1970-05-08 |
| SU489324A3 (ru) | 1975-10-25 |
| RO57886A (pl) | 1975-02-15 |
| IE33602B1 (en) | 1974-08-21 |
| US3646207A (en) | 1972-02-29 |
| DK129124C (pl) | 1975-01-06 |
| YU273769A (en) | 1978-09-18 |
| DK129124B (da) | 1974-08-26 |
| BR6913868D0 (pt) | 1973-02-08 |
| FR2022531B1 (pl) | 1973-07-13 |
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