NO791222L - Fremgangsmaate for fremstilling av tetrahydroalstoninderivater - Google Patents
Fremgangsmaate for fremstilling av tetrahydroalstoninderivaterInfo
- Publication number
- NO791222L NO791222L NO79791222A NO791222A NO791222L NO 791222 L NO791222 L NO 791222L NO 79791222 A NO79791222 A NO 79791222A NO 791222 A NO791222 A NO 791222A NO 791222 L NO791222 L NO 791222L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- acid
- tetrahydroalstonine
- compounds
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 14
- GRTOGORTSDXSFK-DLLGKBFGSA-N tetrahydroalstonine Chemical class C1=CC=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-DLLGKBFGSA-N 0.000 claims description 14
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- -1 piperidino, morpholino, piperazino Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 230000009435 amidation Effects 0.000 claims description 2
- 238000007112 amidation reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010002660 Anoxia Diseases 0.000 description 3
- 241000976983 Anoxia Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- 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 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000007953 anoxia Effects 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 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 2
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000002036 chloroform fraction Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000000506 psychotropic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241001280629 Catharanthus lanceus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000208332 Rauvolfia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000000496 anti-anoxic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000006931 brain damage Effects 0.000 description 1
- 231100000874 brain damage Toxicity 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7811026A FR2422664A1 (fr) | 1978-04-14 | 1978-04-14 | Derives de la tetrahydroalstonine et leur application en therapeutique |
| FR7906055A FR2450835A2 (fr) | 1978-04-14 | 1979-03-09 | Derives de la tetrahydroalstonine et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791222L true NO791222L (no) | 1979-10-16 |
Family
ID=26220552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO79791222A NO791222L (no) | 1978-04-14 | 1979-04-10 | Fremgangsmaate for fremstilling av tetrahydroalstoninderivater |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS54145700A (fr) |
| DE (1) | DE2914805A1 (fr) |
| DK (1) | DK149279A (fr) |
| ES (1) | ES479540A1 (fr) |
| FI (1) | FI791194A (fr) |
| FR (1) | FR2450835A2 (fr) |
| GB (1) | GB2018751A (fr) |
| GR (1) | GR66991B (fr) |
| IL (1) | IL57061A0 (fr) |
| IT (1) | IT1111923B (fr) |
| LU (1) | LU81145A1 (fr) |
| NL (1) | NL7902958A (fr) |
| NO (1) | NO791222L (fr) |
| PT (1) | PT69487A (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2451376B1 (fr) * | 1979-03-14 | 1986-04-18 | Fabre Sa Pierre | Nouveaux derives tetrahydroalstoniques, leur preparation et leur application en tant que medicaments |
| BE881050A (fr) * | 1980-01-09 | 1980-07-09 | Omnichemue | Nouveaux derives du type oxayohimbane, leur procede d'obtention et medicaments les contenant |
| FR2539416B1 (fr) * | 1983-01-14 | 1985-09-27 | Adir | Nouveaux derives oxindoliques, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| SE501156C2 (sv) * | 1993-04-21 | 1994-11-28 | Ellemtel Utvecklings Ab | Referenssignal sammansatt av klocksignal och synkroniseringssignal, anordning och förfarande för synkronisering m.h.a. referenssignal |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1225652B (de) * | 1961-08-01 | 1966-09-29 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von in 1-Stellung substituierten 3, 4, 5, 6-Tetrahydroserpentin-derivaten und von deren Salzen |
-
1979
- 1979-03-09 FR FR7906055A patent/FR2450835A2/fr active Granted
- 1979-04-10 NO NO79791222A patent/NO791222L/no unknown
- 1979-04-10 DK DK149279A patent/DK149279A/da not_active IP Right Cessation
- 1979-04-11 IL IL57061A patent/IL57061A0/xx unknown
- 1979-04-11 FI FI791194A patent/FI791194A/fi not_active Application Discontinuation
- 1979-04-11 IT IT21793/79A patent/IT1111923B/it active
- 1979-04-11 ES ES479540A patent/ES479540A1/es not_active Expired
- 1979-04-11 DE DE19792914805 patent/DE2914805A1/de not_active Withdrawn
- 1979-04-12 NL NL7902958A patent/NL7902958A/xx not_active Application Discontinuation
- 1979-04-12 GR GR58869A patent/GR66991B/el unknown
- 1979-04-12 LU LU81145A patent/LU81145A1/fr unknown
- 1979-04-12 GB GB7912932A patent/GB2018751A/en not_active Withdrawn
- 1979-04-12 PT PT69487A patent/PT69487A/fr unknown
- 1979-04-13 JP JP4595879A patent/JPS54145700A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI791194A (fi) | 1979-10-15 |
| IL57061A0 (en) | 1979-07-25 |
| NL7902958A (nl) | 1979-10-16 |
| ES479540A1 (es) | 1979-07-16 |
| JPS54145700A (en) | 1979-11-14 |
| FR2450835B2 (fr) | 1982-11-19 |
| PT69487A (fr) | 1979-05-01 |
| IT1111923B (it) | 1986-01-13 |
| DK149279A (da) | 1979-10-15 |
| GB2018751A (en) | 1979-10-24 |
| LU81145A1 (fr) | 1980-12-16 |
| DE2914805A1 (de) | 1979-10-18 |
| IT7921793A0 (it) | 1979-04-11 |
| FR2450835A2 (fr) | 1980-10-03 |
| GR66991B (fr) | 1981-05-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3783988T2 (de) | Zyklische enolderivate, herstellung und anwendung. | |
| NO166129B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive tetrahydro-9h-pyrido (3,4-b)indoler. | |
| KR20140051355A (ko) | 이중 활성 H1 역 효능제/5-HT2A 길항제로서의 (티에노[2,3-b][1,5]벤족사제핀-4-일)피페라진-1-일 화합물 | |
| EP0171702A1 (fr) | Dérivés de benzoxazinone, préparation et application | |
| NO158871B (no) | Analogifremgangsmaate for fremstilling av pyridazinderivater. | |
| EP0163537A1 (fr) | Dérivés de la propanone-1 et compositions pharmaceutiques les contenant | |
| US4528289A (en) | Corynantheine derivates, processes for their preparation, and their use | |
| NO791222L (no) | Fremgangsmaate for fremstilling av tetrahydroalstoninderivater | |
| KR20170086636A (ko) | α-아사릴알데히드 에스테르, 이의 제조 방법, 및 이의 응용 | |
| DK168441B1 (da) | [R-(E)]-4-(3-phosphono-2-propenyl)-2-piperazincarboxylsyre, fremgangsmåde til fremstilling deraf, farmaceutisk præparat indeholdende forbindelsen samt anvendelse heraf | |
| KR101582429B1 (ko) | 이중 활성 H1 역 효능제/5-HT2A 길항제로서의 (티에노[2,3-b][1,5]벤족사제핀-4-일)피페라진-1-일 화합물 | |
| EP3517537A1 (fr) | Dérivé deutéré de l-tétrahydropalmatine et son utilisation médicale | |
| WO2017066787A1 (fr) | Composés, compositions et procédés de préparation et d'utilisation de ceux-ci | |
| US4927837A (en) | Derivatives of 3-piperidine carbaldehyde oxime and their use as medicaments | |
| EP3724195A1 (fr) | Dihydrothiénopyrimidines de tétrahydropyrane substituées, et leur utilisation en tant qu'inhibiteurs de la phosphodiestérase | |
| JP2024501828A (ja) | メラノコルチン受容体アゴニスト化合物の結晶形ｉｉおよびその製造方法 | |
| EP0256181A1 (fr) | Dérivés d'amide de l'acide quinoléine-2-carboxylique et leur préparation | |
| CN110655490A (zh) | 一类卤代咪唑类化合物、制备方法及用途 | |
| US8455550B2 (en) | Derivatives of aminocyclobutane or aminocyclobutene, their method of preparation and their use as medical products | |
| US4503058A (en) | Therapeutically useful 3,7a-diazacyclohepta[j,k]fluorene derivatives | |
| US4904670A (en) | Pyridine derivatives having anxiety state or sleep thereapeutic properties | |
| JPH11501043A (ja) | Ｎｏシンターゼの阻害剤として活性を有するアルギニン類縁体 | |
| EP0020885A1 (fr) | Dérivés de 2-hydroxy-6,9-méthano-11-amino-5,6,7,8,9,10-hexahydro-benzocyclooctène, procédé pour leur préparation et compositions pharmaceutiques les contenant | |
| IE52160B1 (en) | Naphthyridine derivatives | |
| DE69424281T2 (de) | Phosphonomethyldipeptide |