SU1053756A3 - Способ получени производных эрголина или их солей - Google Patents
Способ получени производных эрголина или их солей Download PDFInfo
- Publication number
- SU1053756A3 SU1053756A3 SU813263908A SU3263908A SU1053756A3 SU 1053756 A3 SU1053756 A3 SU 1053756A3 SU 813263908 A SU813263908 A SU 813263908A SU 3263908 A SU3263908 A SU 3263908A SU 1053756 A3 SU1053756 A3 SU 1053756A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- urea
- carbonyl
- alkyl
- methoxy
- methyl
- Prior art date
Links
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 title claims abstract description 12
- 150000003839 salts Chemical class 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 230000003993 interaction Effects 0.000 claims abstract description 4
- 238000002955 isolation Methods 0.000 claims abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002184 metal Chemical group 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 description 44
- 230000000694 effects Effects 0.000 description 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 21
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 230000036772 blood pressure Effects 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 230000001077 hypotensive effect Effects 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- -1 6-i-propyl-8 -carboxyergoline Chemical compound 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 4
- 229960002802 bromocriptine Drugs 0.000 description 4
- 229960002474 hydralazine Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 102000003946 Prolactin Human genes 0.000 description 3
- 108010057464 Prolactin Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001263 anti-prolactin effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229940097325 prolactin Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- VFFLQUNAMYWTLJ-UHFFFAOYSA-N carbamoyl isocyanate Chemical compound NC(=O)N=C=O VFFLQUNAMYWTLJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000002895 emetic Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ORBSYPFBZQJNJE-HCGVIMEBSA-N (6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC([C@H]2CC(CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ORBSYPFBZQJNJE-HCGVIMEBSA-N 0.000 description 1
- ZYACKOKSHZQYDS-NTVGDFDMSA-N (6ar,10ar)-9-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)C)C2)=C3C2=CNC3=C1 ZYACKOKSHZQYDS-NTVGDFDMSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- 101100021281 Caenorhabditis elegans lin-8 gene Proteins 0.000 description 1
- 241000252185 Cobitidae Species 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 1
- 208000001287 Galactorrhea Diseases 0.000 description 1
- 206010017600 Galactorrhoea Diseases 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000350158 Prioria balsamifera Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000000095 emetic effect Effects 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 239000000960 hypophysis hormone Substances 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LPMDNOPQLGRDMA-UHFFFAOYSA-N n'-butylmethanediimine Chemical compound CCCCN=C=N LPMDNOPQLGRDMA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
- C07D457/06—Lysergic acid amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8011234 | 1980-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1053756A3 true SU1053756A3 (ru) | 1983-11-07 |
Family
ID=10512588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813263908A SU1053756A3 (ru) | 1980-04-03 | 1981-04-01 | Способ получени производных эрголина или их солей |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS56156279A (enrdf_load_stackoverflow) |
| BE (1) | BE888243A (enrdf_load_stackoverflow) |
| CS (1) | CS221828B2 (enrdf_load_stackoverflow) |
| HU (1) | HU183382B (enrdf_load_stackoverflow) |
| SU (1) | SU1053756A3 (enrdf_load_stackoverflow) |
| UA (1) | UA6027A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA812103B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2173189B (en) * | 1985-02-21 | 1988-04-27 | Maruko Pharmaceutical Co | Ergoline derivatives and salts thereof and pharmaceutical compositions thereof |
| JPS6445652U (enrdf_load_stackoverflow) * | 1987-09-16 | 1989-03-20 | ||
| JPH01123664U (enrdf_load_stackoverflow) * | 1988-02-16 | 1989-08-23 | ||
| EP1925616A1 (en) * | 2006-10-26 | 2008-05-28 | LEK Pharmaceuticals D.D. | Process for the preparation of crystal forms of cabergoline via stable solvates of cabergoline |
-
1981
- 1981-03-30 ZA ZA00812103A patent/ZA812103B/xx unknown
- 1981-03-31 CS CS812388A patent/CS221828B2/cs unknown
- 1981-04-01 SU SU813263908A patent/SU1053756A3/ru active
- 1981-04-01 HU HU81842A patent/HU183382B/hu unknown
- 1981-04-01 UA UA3263908A patent/UA6027A1/uk unknown
- 1981-04-02 JP JP4849181A patent/JPS56156279A/ja active Granted
- 1981-04-02 BE BE0/204351A patent/BE888243A/fr not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| 1. Бюлер К., Пирсон Д. Органические синтезы. М,, Мкр, ч. 2, с. 385. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA812103B (en) | 1982-04-28 |
| JPS6213956B2 (enrdf_load_stackoverflow) | 1987-03-30 |
| JPS56156279A (en) | 1981-12-02 |
| UA6027A1 (uk) | 1994-12-29 |
| CS221828B2 (en) | 1983-04-29 |
| BE888243A (fr) | 1981-10-02 |
| HU183382B (en) | 1984-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4755517A (en) | Derivatives of xanthine, pharmaceutical compositions and methods of use therefor | |
| KR20040087335A (ko) | 질소 함유 복소환 화합물 | |
| EP0066459B1 (en) | Crystalline benzothiazine dioxide salts | |
| US3900477A (en) | 5-amino-and 5-hydrazinodihydropyrroloisoquinoline derivatives | |
| US3978066A (en) | Certain 4,6-dihydropyrrolotriazoline-quinoline derivatives | |
| FR2475548A1 (fr) | Nouveaux derives de quinazoline, leur procede de preparation et leur application en therapeutique | |
| JPH0419996B2 (enrdf_load_stackoverflow) | ||
| EP0245054A1 (en) | Quinoline amides | |
| SU1053756A3 (ru) | Способ получени производных эрголина или их солей | |
| JPS6210519B2 (enrdf_load_stackoverflow) | ||
| SU1189347A3 (ru) | Способ получени производных эрголина | |
| AU2012268815B2 (en) | Delta Crystalline Form of the Arginine Salt of Perindopril, a Process For Its Preparation, and Pharmaceutical Compositions Thereof | |
| NO143459B (no) | Analogifremgangsmaate for fremstilling av fysiologisk aktive 2-fenylimino-imidazolidin-derivater | |
| US3297699A (en) | 5-nitrothiazolyl-dioxo-diazacycloalkanes | |
| US3576808A (en) | N-4-phenyl-1-piperazinylalkyl-5-phenyl-oxazolidinones | |
| US4804751A (en) | Polycyclic hydrocarbon succinimides with psychotropic activity | |
| JPS5846516B2 (ja) | 置換トリフルオロエチルアミン | |
| KR900000565B1 (ko) | 불안해소제 및 우울증 치료제로서의 가교된 비사이클릭 이미드 | |
| DE3314878A1 (de) | Ergolinderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten | |
| FI70412C (fi) | Foerfarande foer framstaellning av ergolinderivat | |
| US5614516A (en) | 12-aminopyridazinopyrroloisoquinoline compounds | |
| US3020288A (en) | Hypotensive compounds | |
| US3174978A (en) | Guanyl hydrazones of dialkylaminophenyl lower alkyl ketones | |
| CS237341B2 (en) | Processing of new basicaly substituted 4-phenyl-4,5,6,7-tetrahydrothien/2,3-c/-pyridine | |
| DE69223422T2 (de) | Benzothiadiazinderivate |