NO136408B - - Google Patents
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- Publication number
- NO136408B NO136408B NO740614A NO740614A NO136408B NO 136408 B NO136408 B NO 136408B NO 740614 A NO740614 A NO 740614A NO 740614 A NO740614 A NO 740614A NO 136408 B NO136408 B NO 136408B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- carbon atoms
- water
- ether
- formaldehyde
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 150000002373 hemiacetals Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical class OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 claims description 5
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 230000000397 acetylating effect Effects 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 45
- 229930040373 Paraformaldehyde Natural products 0.000 description 18
- 229920002866 paraformaldehyde Polymers 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- -1 butynediol Chemical compound 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000003756 stirring Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- BKZLGWURGVCIFE-UHFFFAOYSA-N 1,2,2,2-tetrahydroxyethylazanium;chloride Chemical compound [Cl-].[NH3+]C(O)C(O)(O)O BKZLGWURGVCIFE-UHFFFAOYSA-N 0.000 description 1
- ZXIYZDSEASMXPI-UHFFFAOYSA-N 2-(methylamino)ethane-1,1,1-triol Chemical compound CNCC(O)(O)O ZXIYZDSEASMXPI-UHFFFAOYSA-N 0.000 description 1
- SRUQIHYBCMXLBN-UHFFFAOYSA-N 2-piperazin-1-ylethane-1,1-diol Chemical compound OC(O)CN1CCNCC1 SRUQIHYBCMXLBN-UHFFFAOYSA-N 0.000 description 1
- HJVYNRLADPFPHW-UHFFFAOYSA-N 3-(ethylamino)propane-1,1-diol Chemical compound CCNCCC(O)O HJVYNRLADPFPHW-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001640117 Callaeum Species 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- ZQNDSFIFPAAMQQ-UHFFFAOYSA-N [acetyloxy(diacetyloxymethoxy)methyl] acetate Chemical compound CC(=O)OC(OC(C)=O)OC(OC(C)=O)OC(C)=O ZQNDSFIFPAAMQQ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- LNEDEBJEAPRVTQ-UHFFFAOYSA-N octadecyl(2,2,2-trihydroxyethyl)azanium sulfate Chemical compound S(=O)(=O)([O-])[O-].C(CCCCCCCCCCCCCCCCC)[NH2+]CC(O)(O)O.C(CCCCCCCCCCCCCCCCC)[NH2+]CC(O)(O)O LNEDEBJEAPRVTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000006289 propionylation Effects 0.000 description 1
- 238000010515 propionylation reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CDOAWSMDRRABET-UHFFFAOYSA-M tetrakis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[N+](CCO)(CCO)CCO CDOAWSMDRRABET-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G15/00—Apparatus for electrographic processes using a charge pattern
- G03G15/06—Apparatus for electrographic processes using a charge pattern for developing
- G03G15/08—Apparatus for electrographic processes using a charge pattern for developing using a solid developer, e.g. powder developer
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2308883A DE2308883C3 (de) | 1973-02-23 | 1973-02-23 | 2-Phenylamino-thienylmethyl-imidazoline-(2), Verfahren zur Herstellung derselben und diese enthaltene Arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO740614L NO740614L (no) | 1974-08-26 |
| NO136408B true NO136408B (xx) | 1977-05-23 |
| NO136408C NO136408C (no) | 1977-08-31 |
Family
ID=5872784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO740614A NO136408C (no) | 1973-02-23 | 1974-02-22 | Analogifremgangsm}te for fremstilling av terapeutisk aktive 2-fenylaminoimidazolin (2)-forbindelser |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US3937717A (xx) |
| JP (1) | JPS50121274A (xx) |
| AT (1) | AT331239B (xx) |
| BE (1) | BE811488A (xx) |
| BG (1) | BG25219A3 (xx) |
| CA (1) | CA1020941A (xx) |
| CH (2) | CH584217A5 (xx) |
| CS (2) | CS179438B2 (xx) |
| DD (1) | DD112649A5 (xx) |
| DE (1) | DE2308883C3 (xx) |
| DK (1) | DK137606C (xx) |
| ES (2) | ES423233A1 (xx) |
| FI (1) | FI59802C (xx) |
| FR (1) | FR2218890B1 (xx) |
| GB (1) | GB1455624A (xx) |
| HU (1) | HU167230B (xx) |
| IE (1) | IE39481B1 (xx) |
| IL (1) | IL44266A (xx) |
| NL (1) | NL7402432A (xx) |
| NO (1) | NO136408C (xx) |
| PH (2) | PH10776A (xx) |
| PL (1) | PL90944B1 (xx) |
| RO (2) | RO63035A (xx) |
| SE (1) | SE420489B (xx) |
| SU (2) | SU497772A3 (xx) |
| YU (2) | YU45274A (xx) |
| ZA (1) | ZA741173B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS603065B2 (ja) * | 1976-06-07 | 1985-01-25 | 第一製薬株式会社 | ２―置換エチル―１，３―ジアザシクロアルケン類 |
| CH603643A5 (xx) * | 1976-09-29 | 1978-08-31 | Sandoz Ag | |
| DE2830279A1 (de) * | 1978-07-10 | 1980-01-31 | Boehringer Sohn Ingelheim | 2-eckige klammer auf n-(2'-chlor-4'- methyl-thienyl-3')-n-(cyclopropylmethyl)- amino eckige klammer zu-imidazolin-(2), dessen saeureadditionssalze, dieses enthaltende arzneimittel und verfahren zu seiner herstellung |
| DE2831480A1 (de) * | 1978-07-18 | 1980-01-31 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylamino- imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben |
| DE2951601A1 (de) * | 1979-12-21 | 1981-07-02 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue substituierte 2-phenylaminoimidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben |
| US4287201A (en) * | 1980-03-03 | 1981-09-01 | Merck & Co., Inc. | Anovulatory method and chicken feed compositions |
| US4363751A (en) * | 1980-08-04 | 1982-12-14 | Merck & Co., Inc. | Catalyst for the preparation of 4-cyanothiazole and process for preparing the catalyst |
| DE3200258A1 (de) * | 1982-01-07 | 1983-07-21 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Substituierte 1-benzoyl-2-phenylimino-imidazolidine, deren saeureadditionssalze, verfahren zu deren herstellung und diese enthaltende arzneimittel |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3236857A (en) * | 1961-10-09 | 1966-02-22 | Boehringer Sohn Ingelheim | 2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products |
| US3147270A (en) * | 1961-11-03 | 1964-09-01 | Warner Lambert Pharmaceutical | Substituted 2-imidazolines |
| BE754820R (fr) * | 1969-08-13 | 1971-02-15 | Schering Ag | Nouveaux derives de pyrimidine, leurs procedes de preparation et leurs |
| US3746724A (en) * | 1970-04-13 | 1973-07-17 | Ciba Geigy Corp | 3-guanidinoalkyl-thiophenes |
| DD95843A5 (xx) * | 1971-01-21 | 1973-02-20 |
-
1973
- 1973-02-23 DE DE2308883A patent/DE2308883C3/de not_active Expired
-
1974
- 1974-02-01 AT AT79274*#A patent/AT331239B/de not_active IP Right Cessation
- 1974-02-11 US US05/441,451 patent/US3937717A/en not_active Expired - Lifetime
- 1974-02-14 PH PH15507A patent/PH10776A/en unknown
- 1974-02-14 ES ES423233A patent/ES423233A1/es not_active Expired
- 1974-02-14 ES ES423232A patent/ES423232A1/es not_active Expired
- 1974-02-19 SU SU1998097A patent/SU497772A3/ru active
- 1974-02-19 RO RO7400077744A patent/RO63035A/ro unknown
- 1974-02-19 RO RO7484328A patent/RO68649A/ro unknown
- 1974-02-19 DD DD176669A patent/DD112649A5/xx unknown
- 1974-02-19 SU SU1998274A patent/SU495838A3/ru active
- 1974-02-20 FI FI495/74A patent/FI59802C/fi active
- 1974-02-20 CA CA193,072A patent/CA1020941A/en not_active Expired
- 1974-02-21 BG BG025855A patent/BG25219A3/xx unknown
- 1974-02-21 YU YU00452/74A patent/YU45274A/xx unknown
- 1974-02-21 HU HUBO1486A patent/HU167230B/hu unknown
- 1974-02-22 SE SE7402399A patent/SE420489B/xx unknown
- 1974-02-22 IL IL44266A patent/IL44266A/en unknown
- 1974-02-22 GB GB820274A patent/GB1455624A/en not_active Expired
- 1974-02-22 JP JP49021338A patent/JPS50121274A/ja active Pending
- 1974-02-22 FR FR7406149A patent/FR2218890B1/fr not_active Expired
- 1974-02-22 NL NL7402432A patent/NL7402432A/xx not_active Application Discontinuation
- 1974-02-22 IE IE372/74A patent/IE39481B1/xx unknown
- 1974-02-22 DK DK96074A patent/DK137606C/da active
- 1974-02-22 ZA ZA00741173A patent/ZA741173B/xx unknown
- 1974-02-22 CS CS7400001346A patent/CS179438B2/cs unknown
- 1974-02-22 NO NO740614A patent/NO136408C/no unknown
- 1974-02-22 BE BE141318A patent/BE811488A/xx unknown
- 1974-02-22 PL PL1974169029A patent/PL90944B1/pl unknown
- 1974-02-25 CH CH263774A patent/CH584217A5/xx not_active IP Right Cessation
- 1974-02-25 CH CH263674A patent/CH584218A5/xx not_active IP Right Cessation
- 1974-12-22 CS CS7600001986A patent/CS179449B2/cs unknown
-
1976
- 1976-09-13 PH PH18897A patent/PH15346A/en unknown
-
1980
- 1980-06-12 YU YU01571/80A patent/YU157180A/xx unknown
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