DK141531B - Analogifremgangsmåde til fremstilling af 1-metyl-9,10-dihydro-d-lysergsyreallylamid eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af 1-metyl-9,10-dihydro-d-lysergsyreallylamid eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK141531B DK141531B DK51373AA DK51373A DK141531B DK 141531 B DK141531 B DK 141531B DK 51373A A DK51373A A DK 51373AA DK 51373 A DK51373 A DK 51373A DK 141531 B DK141531 B DK 141531B
- Authority
- DK
- Denmark
- Prior art keywords
- lysergic acid
- acid
- methyl
- dihydro
- lysergic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 239000002253 acid Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 21
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- -1 lysergic acid halides Chemical class 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- UUYMPWWTAQZUQB-QMTHXVAHSA-N (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carbohydrazide Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(=O)NN)=C3C2=CNC3=C1 UUYMPWWTAQZUQB-QMTHXVAHSA-N 0.000 description 1
- NCIHPOHJJSIWSC-QMTHXVAHSA-N (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl azide Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(=O)N=[N+]=[N-])=C3C2=CNC3=C1 NCIHPOHJJSIWSC-QMTHXVAHSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001146155 Emilia Species 0.000 description 1
- 235000002139 Emilia sonchifolia Nutrition 0.000 description 1
- 241001000161 Mago Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-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
- 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 229940124572 antihypotensive agent Drugs 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229960003133 ergot alkaloid Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- RNHDWLRHUJZABX-IAQYHMDHSA-N methyl (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)OC)C2)=C3C2=CNC3=C1 RNHDWLRHUJZABX-IAQYHMDHSA-N 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000016160 smooth muscle contraction Effects 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
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000005406 washing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- C07D457/08—Lysergic acid amides in which the amide nitrogen is a member of a heterocyclic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001187 | 1972-02-04 | ||
| HUGO001186 | 1972-02-04 | ||
| HUGO001186 HU164051B (enExample) | 1972-02-04 | 1972-02-04 | |
| HUGO001187 HU163546B (enExample) | 1972-02-04 | 1972-02-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141531B true DK141531B (da) | 1980-04-14 |
| DK141531C DK141531C (enExample) | 1980-10-06 |
Family
ID=26318474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK51373AA DK141531B (da) | 1972-02-04 | 1973-01-31 | Analogifremgangsmåde til fremstilling af 1-metyl-9,10-dihydro-d-lysergsyreallylamid eller syreadditionssalte deraf. |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5221516B2 (enExample) |
| AU (1) | AU475943B2 (enExample) |
| BE (1) | BE794888A (enExample) |
| BG (1) | BG22832A3 (enExample) |
| CA (1) | CA994342A (enExample) |
| CH (1) | CH589079A5 (enExample) |
| CS (1) | CS191212B2 (enExample) |
| DD (1) | DD104299A5 (enExample) |
| DE (1) | DE2305514A1 (enExample) |
| DK (1) | DK141531B (enExample) |
| EG (1) | EG10823A (enExample) |
| FI (1) | FI54118C (enExample) |
| FR (1) | FR2190440B1 (enExample) |
| GB (1) | GB1401155A (enExample) |
| IL (1) | IL41409A (enExample) |
| NL (1) | NL178256C (enExample) |
| NO (1) | NO133670C (enExample) |
| SE (1) | SE421424B (enExample) |
| SU (1) | SU468419A3 (enExample) |
| YU (1) | YU36730B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU169073B (enExample) * | 1974-05-28 | 1976-09-28 | ||
| HU168914B (enExample) * | 1974-07-30 | 1976-08-28 | ||
| HU172649B (hu) * | 1975-04-24 | 1978-11-28 | Gyogyszerkutato Intezet | Sposob poluchenija novykh biologicheski aktivnykh lizergamidov |
| DE2802023A1 (de) * | 1977-01-28 | 1978-08-03 | Sandoz Ag | Neue ergotderivate, ihre herstellung und verwendung |
| JPH0438472U (enExample) * | 1990-07-31 | 1992-03-31 | ||
| IT1260156B (it) * | 1992-08-03 | 1996-03-28 | Fidia Spa | Derivati dell'acido neuraminico |
| KR20140042868A (ko) * | 2011-06-23 | 2014-04-07 | 맵 파마슈티컬스, 인코포레이티드 | 신규한 플루오로에르골린 유사체 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH475252A (de) * | 1966-02-08 | 1969-07-15 | Sandoz Ag | Verfahren zur Herstellung neuer Lysergsäure-Derivate |
| AT291446B (de) * | 1968-11-22 | 1971-07-12 | Richter Gedeon Vegyeszet | Verfahren zur Herstellung von neuen Apovincaminsäureamiden |
-
1973
- 1973-01-29 IL IL41409A patent/IL41409A/en unknown
- 1973-01-31 SE SE7301353A patent/SE421424B/xx unknown
- 1973-01-31 NL NLAANVRAGE7301369,A patent/NL178256C/xx not_active IP Right Cessation
- 1973-01-31 DK DK51373AA patent/DK141531B/da not_active IP Right Cessation
- 1973-02-01 AU AU51633/73A patent/AU475943B2/en not_active Expired
- 1973-02-01 EG EG41/73A patent/EG10823A/xx active
- 1973-02-01 FI FI303/73A patent/FI54118C/fi active
- 1973-02-02 YU YU0266/73A patent/YU36730B/xx unknown
- 1973-02-02 GB GB522073A patent/GB1401155A/en not_active Expired
- 1973-02-02 CH CH152173A patent/CH589079A5/xx not_active IP Right Cessation
- 1973-02-02 SU SU1880877A patent/SU468419A3/ru active
- 1973-02-02 FR FR7303737A patent/FR2190440B1/fr not_active Expired
- 1973-02-02 BE BE794888D patent/BE794888A/xx not_active IP Right Cessation
- 1973-02-02 DD DD168642A patent/DD104299A5/xx unknown
- 1973-02-02 CA CA162,796A patent/CA994342A/en not_active Expired
- 1973-02-02 CS CS73816A patent/CS191212B2/cs unknown
- 1973-02-02 NO NO430/73A patent/NO133670C/no unknown
- 1973-02-03 BG BG022616A patent/BG22832A3/xx unknown
- 1973-02-05 DE DE2305514A patent/DE2305514A1/de not_active Ceased
- 1973-02-05 JP JP48013871A patent/JPS5221516B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| YU26673A (en) | 1982-02-25 |
| FI54118C (fi) | 1978-10-10 |
| YU36730B (en) | 1984-08-31 |
| NO133670C (enExample) | 1976-06-09 |
| CA994342A (en) | 1976-08-03 |
| AU475943B2 (en) | 1976-09-09 |
| DK141531C (enExample) | 1980-10-06 |
| JPS5221516B2 (enExample) | 1977-06-10 |
| FR2190440A1 (enExample) | 1974-02-01 |
| NL178256C (nl) | 1986-02-17 |
| IL41409A (en) | 1977-04-29 |
| AU5163373A (en) | 1974-08-01 |
| IL41409A0 (en) | 1973-03-30 |
| NL178256B (nl) | 1985-09-16 |
| JPS4886900A (enExample) | 1973-11-15 |
| DD104299A5 (enExample) | 1974-03-05 |
| BE794888A (fr) | 1973-05-29 |
| FI54118B (fi) | 1978-06-30 |
| CS191212B2 (en) | 1979-06-29 |
| EG10823A (en) | 1976-07-31 |
| DE2305514A1 (de) | 1973-08-16 |
| BG22832A3 (bg) | 1977-04-20 |
| NO133670B (enExample) | 1976-03-01 |
| GB1401155A (en) | 1975-07-16 |
| SE421424B (sv) | 1981-12-21 |
| NL7301369A (enExample) | 1973-08-07 |
| CH589079A5 (enExample) | 1977-06-30 |
| SU468419A3 (ru) | 1975-04-25 |
| FR2190440B1 (enExample) | 1976-09-03 |
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| PBP | Patent lapsed |