NO119741B - - Google Patents
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- Publication number
- NO119741B NO119741B NO169188A NO16918867A NO119741B NO 119741 B NO119741 B NO 119741B NO 169188 A NO169188 A NO 169188A NO 16918867 A NO16918867 A NO 16918867A NO 119741 B NO119741 B NO 119741B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- atoms
- heated
- general formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- PAMWIQZMLLUFBP-UHFFFAOYSA-N 1-aminopiperidine-2,6-dione Chemical class NN1C(=O)CCCC1=O PAMWIQZMLLUFBP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- -1 dicarboxylic acid imide Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- VVPXCQJEIWWMEH-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)N1C(=O)CCC1=O VVPXCQJEIWWMEH-UHFFFAOYSA-N 0.000 claims 1
- FEFFSKLJNYRHQN-VIFPVBQESA-N N-phthaloyl-L-glutamic acid Chemical group C1=CC=C2C(=O)N([C@@H](CCC(=O)O)C(O)=O)C(=O)C2=C1 FEFFSKLJNYRHQN-VIFPVBQESA-N 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 150000008064 anhydrides Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FEFFSKLJNYRHQN-UHFFFAOYSA-N 2-Phthalimidoglutaricacid Chemical compound C1=CC=C2C(=O)N(C(CCC(=O)O)C(O)=O)C(=O)C2=C1 FEFFSKLJNYRHQN-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013922 glutamic acid Nutrition 0.000 description 3
- 239000004220 glutamic acid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 description 1
- KBYGMAHGQLUGQE-VIFPVBQESA-N CCOC(CC[C@@H](C(OCC)=O)NC(CCC(O)=O)=O)=O Chemical compound CCOC(CC[C@@H](C(OCC)=O)NC(CCC(O)=O)=O)=O KBYGMAHGQLUGQE-VIFPVBQESA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 241001062472 Stokellia anisodon Species 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2085166 | 1966-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119741B true NO119741B (en, 2012) | 1970-06-29 |
Family
ID=11173007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169188A NO119741B (en, 2012) | 1966-07-29 | 1967-07-27 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3557118A (en, 2012) |
| AT (1) | AT278254B (en, 2012) |
| BE (1) | BE702014A (en, 2012) |
| DE (1) | DE1695752C3 (en, 2012) |
| ES (1) | ES343513A1 (en, 2012) |
| FI (1) | FI47767C (en, 2012) |
| GR (1) | GR36620B (en, 2012) |
| IL (1) | IL28388A (en, 2012) |
| NO (1) | NO119741B (en, 2012) |
| SE (1) | SE340284B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR6915443D0 (pt) * | 1969-07-18 | 1973-03-13 | Farmaceutici Italia | Processo para a preparacao de derivados de ergolina |
| US3957785A (en) * | 1971-12-02 | 1976-05-18 | Societa' Farmaceutici Italia S.P.A. | Bβ-Pyrimidino-aminomethyl-10α-ergoline and 10α-methoxyergoline derivatives |
| CS171480B1 (en, 2012) * | 1974-03-19 | 1976-10-29 | ||
| CS177530B1 (en) * | 1974-07-19 | 1977-07-29 | Miroslav Semonsky | New nbeta-substituted derivatives of b-beta-aminoethyl-ergoline-i their salts and methods for the production thereof |
| US4348392A (en) * | 1974-07-19 | 1982-09-07 | Sandoz Ltd. | 8α-Substituted ergoline-I derivatives |
| US3985752A (en) * | 1974-12-06 | 1976-10-12 | Eli Lilly And Company | 6-Methyl-8-(substituted) methylergolines |
| IT1064473B (it) * | 1976-11-24 | 1985-02-18 | Simes | Sulfamoil derivati dell'8-beta-amminometilergolina |
| FR2421176A1 (fr) * | 1978-03-29 | 1979-10-26 | Sandoz Sa | Nouveaux derives de l'ergot de seigle, leur preparation et leur application comme medicaments |
| HU190105B (en) * | 1983-06-03 | 1986-08-28 | Gyogyszerkutato Intezet | Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts |
-
1967
- 1967-07-24 DE DE1695752A patent/DE1695752C3/de not_active Expired
- 1967-07-24 IL IL28388A patent/IL28388A/en unknown
- 1967-07-25 GR GR670136620A patent/GR36620B/el unknown
- 1967-07-25 US US655755A patent/US3557118A/en not_active Expired - Lifetime
- 1967-07-25 AT AT690467A patent/AT278254B/de not_active IP Right Cessation
- 1967-07-27 FI FI672059A patent/FI47767C/fi active
- 1967-07-27 NO NO169188A patent/NO119741B/no unknown
- 1967-07-28 SE SE10929/67*A patent/SE340284B/xx unknown
- 1967-07-28 BE BE702014D patent/BE702014A/xx unknown
- 1967-07-28 ES ES343513A patent/ES343513A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE340284B (en, 2012) | 1971-11-15 |
| FI47767B (en, 2012) | 1973-11-30 |
| DE1695752A1 (de) | 1972-03-30 |
| DE1695752B2 (de) | 1973-10-31 |
| DE1695752C3 (de) | 1974-06-06 |
| IL28388A (en) | 1971-11-29 |
| FI47767C (fi) | 1974-03-11 |
| GR36620B (el) | 1969-02-26 |
| AT278254B (de) | 1970-01-26 |
| ES343513A1 (es) | 1968-10-16 |
| BE702014A (en, 2012) | 1968-01-29 |
| US3557118A (en) | 1971-01-19 |
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