FI59251C - Foerfarande foer framstaellning av en ny 5-(4-allyl-1-piperazinyl)karbonyloxi-6-(7-klor-1,8-naftyridin-2-yl)-7-oxi-2,3-6,7-tetrahydro-5h-oxatino(1,4)(2,3-c)pyrrol anvaendbar saosom ett laekemedel - Google Patents
Foerfarande foer framstaellning av en ny 5-(4-allyl-1-piperazinyl)karbonyloxi-6-(7-klor-1,8-naftyridin-2-yl)-7-oxi-2,3-6,7-tetrahydro-5h-oxatino(1,4)(2,3-c)pyrrol anvaendbar saosom ett laekemedel Download PDFInfo
- Publication number
- FI59251C FI59251C FI753126A FI753126A FI59251C FI 59251 C FI59251 C FI 59251C FI 753126 A FI753126 A FI 753126A FI 753126 A FI753126 A FI 753126A FI 59251 C FI59251 C FI 59251C
- Authority
- FI
- Finland
- Prior art keywords
- chloro
- naphthyridin
- oxatino
- tetrahydro
- piperazinyl
- Prior art date
Links
- -1 4-ALLYL-1-PIPERAZINYL Chemical class 0.000 title claims description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 241000699670 Mus sp. Species 0.000 description 14
- 239000000126 substance Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 206010010904 Convulsion Diseases 0.000 description 7
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000036461 convulsion Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000006742 locomotor activity Effects 0.000 description 3
- 150000003892 tartrate salts Chemical class 0.000 description 3
- HRXBYPUUCBEZAS-UHFFFAOYSA-N 7-chloro-1,8-naphthyridin-2-amine Chemical compound C1=CC(Cl)=NC2=NC(N)=CC=C21 HRXBYPUUCBEZAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000016571 aggressive behavior Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 208000012761 aggressive behavior Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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 to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7436962A FR2290208A1 (fr) | 1974-11-07 | 1974-11-07 | Nouveaux derives de l'oxathiinno(1,4)(2,3-c)pyrrole, leur preparation et les compositions qui les contiennent |
| FR7436962 | 1974-11-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI753126A7 FI753126A7 (is") | 1976-05-08 |
| FI59251B FI59251B (fi) | 1981-03-31 |
| FI59251C true FI59251C (fi) | 1981-07-10 |
Family
ID=9144747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI753126A FI59251C (fi) | 1974-11-07 | 1975-11-07 | Foerfarande foer framstaellning av en ny 5-(4-allyl-1-piperazinyl)karbonyloxi-6-(7-klor-1,8-naftyridin-2-yl)-7-oxi-2,3-6,7-tetrahydro-5h-oxatino(1,4)(2,3-c)pyrrol anvaendbar saosom ett laekemedel |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4021554A (is") |
| JP (2) | JPS6029716B2 (is") |
| AR (2) | AR214045A1 (is") |
| AT (1) | AT342603B (is") |
| AU (1) | AU503381B2 (is") |
| BE (1) | BE835324A (is") |
| CA (1) | CA1054599A (is") |
| CH (2) | CH608238A5 (is") |
| CS (1) | CS191285B2 (is") |
| DD (1) | DD122541A5 (is") |
| DE (1) | DE2550163C2 (is") |
| DK (1) | DK499175A (is") |
| ES (2) | ES442442A1 (is") |
| FI (1) | FI59251C (is") |
| FR (1) | FR2290208A1 (is") |
| GB (1) | GB1466829A (is") |
| HU (1) | HU170500B (is") |
| IE (1) | IE42030B1 (is") |
| IL (1) | IL48422A (is") |
| LU (1) | LU73737A1 (is") |
| NL (1) | NL7512731A (is") |
| NO (1) | NO143534C (is") |
| OA (1) | OA05141A (is") |
| PH (1) | PH14755A (is") |
| SE (1) | SE419222B (is") |
| SU (2) | SU576949A3 (is") |
| YU (2) | YU281175A (is") |
| ZA (1) | ZA756953B (is") |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1072557A (fr) * | 1976-02-20 | 1980-02-26 | Rhone-Poulenc Industries | Derives du dithiepinno (1,4)(2,3-c) pyrrole, leur preparation et les compositions qui les contiennent |
| FR2525605A1 (fr) * | 1982-04-22 | 1983-10-28 | Rhone Poulenc Sante | Nouveaux derives du dithiinno (1,4) (2,3-c) pyrrole, leur preparation et les medicaments qui les contiennent |
| FR2607504B1 (fr) * | 1986-12-02 | 1989-01-27 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| NZ581544A (en) * | 2007-05-31 | 2012-06-29 | Glycan Biosciences | Sulphated xylans for treatment or prophylaxis of respiratory diseases |
-
1973
- 1973-11-05 ZA ZA00756953A patent/ZA756953B/xx unknown
-
1974
- 1974-11-07 FR FR7436962A patent/FR2290208A1/fr active Granted
-
1975
- 1975-10-20 OA OA55642A patent/OA05141A/xx unknown
- 1975-10-30 NL NL7512731A patent/NL7512731A/xx not_active Application Discontinuation
- 1975-11-05 PH PH17742A patent/PH14755A/en unknown
- 1975-11-05 US US05/628,927 patent/US4021554A/en not_active Expired - Lifetime
- 1975-11-05 IL IL48422A patent/IL48422A/xx unknown
- 1975-11-05 GB GB4593675A patent/GB1466829A/en not_active Expired
- 1975-11-05 CA CA239060A patent/CA1054599A/fr not_active Expired
- 1975-11-05 HU HURO867A patent/HU170500B/hu unknown
- 1975-11-05 JP JP50132199A patent/JPS6029716B2/ja not_active Expired
- 1975-11-05 AU AU86332/75A patent/AU503381B2/en not_active Expired
- 1975-11-05 IE IE2413/75A patent/IE42030B1/en unknown
- 1975-11-05 DD DD189259A patent/DD122541A5/xx unknown
- 1975-11-06 SE SE7512476A patent/SE419222B/xx unknown
- 1975-11-06 AR AR261090A patent/AR214045A1/es active
- 1975-11-06 LU LU73737A patent/LU73737A1/xx unknown
- 1975-11-06 CH CH1437775A patent/CH608238A5/xx not_active IP Right Cessation
- 1975-11-06 DK DK499175A patent/DK499175A/da unknown
- 1975-11-06 BE BE161651A patent/BE835324A/xx not_active IP Right Cessation
- 1975-11-06 SU SU7502186405A patent/SU576949A3/ru active
- 1975-11-06 YU YU02811/75A patent/YU281175A/xx unknown
- 1975-11-06 NO NO753712A patent/NO143534C/no unknown
- 1975-11-06 CH CH782118A patent/CH608808A5/xx not_active IP Right Cessation
- 1975-11-07 CS CS757509A patent/CS191285B2/cs unknown
- 1975-11-07 FI FI753126A patent/FI59251C/fi not_active IP Right Cessation
- 1975-11-07 ES ES442442A patent/ES442442A1/es not_active Expired
- 1975-11-07 ES ES442441A patent/ES442441A1/es not_active Expired
- 1975-11-07 DE DE2550163A patent/DE2550163C2/de not_active Expired
- 1975-11-07 AT AT848575A patent/AT342603B/de not_active IP Right Cessation
-
1976
- 1976-06-21 SU SU762370948A patent/SU615860A3/ru active
- 1976-07-26 AR AR264076A patent/AR214400A1/es active
-
1982
- 1982-05-20 YU YU01080/82A patent/YU108082A/xx unknown
-
1985
- 1985-02-27 JP JP60036703A patent/JPS60222484A/ja active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RHONE- POULENC INDUSTRIES |