IL32853A - 5,11-dihydro-6h-pyrido(2,3-b)-(1,4)benzodiazepine-6-ones substituted in 11-position and processes for the production thereof - Google Patents
5,11-dihydro-6h-pyrido(2,3-b)-(1,4)benzodiazepine-6-ones substituted in 11-position and processes for the production thereofInfo
- Publication number
- IL32853A IL32853A IL32853A IL3285369A IL32853A IL 32853 A IL32853 A IL 32853A IL 32853 A IL32853 A IL 32853A IL 3285369 A IL3285369 A IL 3285369A IL 32853 A IL32853 A IL 32853A
- Authority
- IL
- Israel
- Prior art keywords
- dihydro
- pyrido
- compounds
- methyl
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- MIRBIZDDMSFTKY-UHFFFAOYSA-N 5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical group O=C1NC2=CC=CN=C2NC2=CC=CC=C12 MIRBIZDDMSFTKY-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 75
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- -1 piperazino group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000003826 tablet Substances 0.000 claims description 19
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 239000008298 dragée Substances 0.000 claims description 11
- 239000007940 sugar coated tablet Substances 0.000 claims description 11
- 229940049706 benzodiazepine Drugs 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 8
- 239000000829 suppository Substances 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003610 charcoal Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
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- 238000001802 infusion Methods 0.000 claims description 2
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 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 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000005179 haloacetyl group Chemical group 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 108010068487 targesin Proteins 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681795183 DE1795183B1 (de) | 1968-08-20 | 1968-08-20 | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32853A0 IL32853A0 (en) | 1969-11-12 |
| IL32853A true IL32853A (en) | 1972-06-28 |
Family
ID=5708088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32853A IL32853A (en) | 1968-08-20 | 1969-08-19 | 5,11-dihydro-6h-pyrido(2,3-b)-(1,4)benzodiazepine-6-ones substituted in 11-position and processes for the production thereof |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US3660380A (is") |
| AT (1) | AT289127B (is") |
| BE (1) | BE737748A (is") |
| BG (1) | BG15574A3 (is") |
| BR (1) | BR6911739D0 (is") |
| CH (1) | CH511241A (is") |
| CS (1) | CS163742B2 (is") |
| DE (1) | DE1795183B1 (is") |
| DK (1) | DK123600B (is") |
| ES (1) | ES370394A1 (is") |
| FI (1) | FI49515C (is") |
| FR (1) | FR2016009B1 (is") |
| GB (1) | GB1277132A (is") |
| IE (1) | IE33269B1 (is") |
| IL (1) | IL32853A (is") |
| IT (1) | IT7949451A0 (is") |
| MY (1) | MY7500209A (is") |
| NL (1) | NL142683B (is") |
| NO (1) | NO124073B (is") |
| PL (1) | PL69767B1 (is") |
| RO (1) | RO56172A (is") |
| SE (1) | SE352638B (is") |
| YU (1) | YU34038B (is") |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI50242C (fi) * | 1969-07-18 | 1976-01-12 | Thomae Gmbh Dr K | Menetelmä valmistaa farmakologisesti aktiivisia uusia diallyyliaminoal kanoyylidibenso- tai pyridobenso-diatsepiineja ja niiden happoadditios uoloja. |
| DE2424811C3 (de) * | 1974-05-22 | 1981-08-20 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DE2724434A1 (de) * | 1977-05-31 | 1979-02-22 | Thomae Gmbh Dr K | Neue, in 11-stellung substituierte 5,11-dihydro-6h-pyrido eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4210648A (en) * | 1977-05-31 | 1980-07-01 | Boehringer Ingelheim Gmbh | II-Aminoacyl-5,11-dihydro-6H-pyrido(2,3-B) (1,4)benzodiazepin-6-ones and salts thereof |
| DE2724478C2 (de) * | 1977-05-31 | 1986-05-22 | Dr. Karl Thomae Gmbh, 7950 Biberach | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2724501A1 (de) * | 1977-05-31 | 1978-12-21 | Thomae Gmbh Dr K | Neue, in 11-stellung substituierte 5,11-dihydro-6h-pyrido eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-6- one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB2053187A (en) * | 1979-07-09 | 1981-02-04 | Grissmann Chem Ltd | Process for preparing pyrenzepine |
| EP0064775A1 (de) * | 1979-08-03 | 1982-11-17 | Byk Gulden Lomberg Chemische Fabrik GmbH | Substituierte Tetraazatricyclen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US4404137A (en) * | 1979-10-16 | 1983-09-13 | Lilly Industries Limited | Pyrazolo [3,4-b][1,5]benzodiazepine compounds |
| IT1130973B (it) * | 1980-03-17 | 1986-06-18 | Microsules Argentina Sa De S C | Processo per la preparazione di derivati di 5,11-di-idro-6h-pirido(2,3-b) (1,4)-benzodiazepin-6-one,derivati finali ed intermedi di sintesi in tal modo ottenuti |
| IL62792A (en) * | 1980-05-07 | 1985-02-28 | Byk Gulden Lomberg Chem Fab | Acylated dihydrothienodiazepinone compounds,process for their preparation,and medicaments containing them |
| US4381301A (en) * | 1980-05-07 | 1983-04-26 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted tricyclic thieno compounds, their synthesis, their use, their compositions and their medicaments |
| DE3113094A1 (de) * | 1981-04-01 | 1982-10-21 | Basf Ag, 6700 Ludwigshafen | 5,6-dihydro-11-alkylen-morphantridin-6-one, ihre herstellung und diese enthaltende arzneimittel |
| DE3204401A1 (de) | 1982-02-09 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| IT1212742B (it) * | 1983-05-17 | 1989-11-30 | Dompe Farmaceutici Spa | Derivati dibenzo [1,4]diazepinonici pirido [1,4] benzodiazepinonici,pirido [1,5] benzodiazepinonici e loro attivita' farmacologica |
| DD236731B3 (de) * | 1983-10-19 | 1992-12-10 | Dresden Arzneimittel | Verfahren zur herstellung von neuen in 5-stellung substituierten 5,10-dihydro-11h-dibenzo|b,e¨|1,4¨diazepin-11-onen |
| DE3403693A1 (de) * | 1984-02-03 | 1985-08-08 | Dr. Karl Thomae Gmbh, 7950 Biberach | Verwendung von pirenzepin, seinen salzen bzw. pirenzepinhaltigen arzneimitteln zur behandlung des colon irritabile |
| DE3409237A1 (de) * | 1984-03-14 | 1985-09-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| WO1986006278A1 (en) * | 1985-04-19 | 1986-11-06 | University Patents, Inc. | Method for treating obstructive airway diseases |
| DE3626095A1 (de) * | 1986-07-31 | 1988-02-11 | Thomae Gmbh Dr K | Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3643666A1 (de) * | 1986-12-20 | 1988-06-30 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3726908A1 (de) * | 1987-08-13 | 1989-02-23 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3820347A1 (de) * | 1988-06-15 | 1989-12-21 | Thomae Gmbh Dr K | Verwendung von in 11-stellung substituierten 5,11-dihydro-6h-pyrido(2,3-b) (1,4)benzodiazepin-6-onen zur behandlung von bradycardien und bradyarrhythmien in der human- und veterinaermedizin |
| US5298508A (en) * | 1988-07-19 | 1994-03-29 | The United States Of America As Represented By The Department Of Health And Human Services | Irreversible inhibitors of adenosine receptors |
| DE3919076A1 (de) * | 1989-06-10 | 1990-12-13 | Thomae Gmbh Dr K | Mittel zur behandlung von erkrankungen des zentralnervensystems und zur foerderung der cerebralen durchblutung |
| US5324832A (en) * | 1991-07-03 | 1994-06-28 | The United States Of America As Represented By The Department Of Health And Human Services | Muscarinic antagonists |
| US5716952A (en) * | 1992-03-18 | 1998-02-10 | Allergan | Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists |
| AU2603197A (en) | 1996-04-10 | 1997-10-29 | United States Of America, Represented By The Secretary, Department Of Health And Human Services, The | Use of an a1 adenosine receptor agonist to treat cerebral ischaemia |
| JP5020819B2 (ja) | 2004-07-16 | 2012-09-05 | プロテオシス・アーゲー | 細胞保護剤としての、ｐａｒｐ及びｓｉｒ調節活性を有するムスカリンアンタゴニスト |
| US7893053B2 (en) | 2006-06-16 | 2011-02-22 | Theracos, Inc. | Treating psychological conditions using muscarinic receptor M1 antagonists |
| US8748419B2 (en) | 2006-06-16 | 2014-06-10 | Theracos, Inc. | Treating obesity with muscarinic receptor M1 antagonists |
| FR2909700B1 (fr) | 2006-12-12 | 2010-10-15 | Dalo Freres Soc | Ensemble support pour un element de toiture,abri comprenant un tel ensemble support et procede de montage d'un tel abri |
| CA2691844A1 (en) * | 2007-07-02 | 2009-01-08 | Ac Immune S.A. | Therapeutic compound |
| WO2010081825A2 (en) | 2009-01-13 | 2010-07-22 | Proteosys Ag | Pirenzepine as an agent in cancer treatment |
-
1968
- 1968-08-20 DE DE19681795183 patent/DE1795183B1/de active Pending
-
1969
- 1969-07-24 RO RO60619A patent/RO56172A/ro unknown
- 1969-07-26 BG BG012746A patent/BG15574A3/bg unknown
- 1969-07-30 FI FI692259A patent/FI49515C/fi active
- 1969-08-07 US US848345A patent/US3660380A/en not_active Expired - Lifetime
- 1969-08-11 ES ES370394A patent/ES370394A1/es not_active Expired
- 1969-08-13 IE IE1143/69A patent/IE33269B1/xx unknown
- 1969-08-19 CH CH1254069A patent/CH511241A/de not_active IP Right Cessation
- 1969-08-19 AT AT796069A patent/AT289127B/de not_active IP Right Cessation
- 1969-08-19 NO NO3362/69A patent/NO124073B/no unknown
- 1969-08-19 PL PL1969135431A patent/PL69767B1/pl unknown
- 1969-08-19 DK DK443569AA patent/DK123600B/da not_active IP Right Cessation
- 1969-08-19 IL IL32853A patent/IL32853A/en unknown
- 1969-08-20 YU YU2152/69A patent/YU34038B/xx unknown
- 1969-08-20 FR FR696928590A patent/FR2016009B1/fr not_active Expired
- 1969-08-20 NL NL696912652A patent/NL142683B/xx not_active IP Right Cessation
- 1969-08-20 CS CS5773A patent/CS163742B2/cs unknown
- 1969-08-20 BR BR211739/69A patent/BR6911739D0/pt unknown
- 1969-08-20 BE BE737748D patent/BE737748A/xx not_active IP Right Cessation
- 1969-08-20 GB GB41597/69A patent/GB1277132A/en not_active Expired
- 1969-08-20 SE SE11569/69A patent/SE352638B/xx unknown
-
1972
- 1972-02-09 US US00224974A patent/US3743734A/en not_active Expired - Lifetime
-
1975
- 1975-12-30 MY MY209/75A patent/MY7500209A/xx unknown
-
1979
- 1979-06-18 IT IT7949451A patent/IT7949451A0/it unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH511241A (de) | 1971-08-15 |
| DK123600B (da) | 1972-07-10 |
| FI49515C (fi) | 1975-07-10 |
| NL142683B (nl) | 1974-07-15 |
| YU215269A (en) | 1978-05-15 |
| DE1795183B1 (de) | 1972-07-20 |
| FR2016009B1 (is") | 1973-08-10 |
| FI49515B (is") | 1975-04-01 |
| MY7500209A (en) | 1975-12-31 |
| YU34038B (en) | 1978-10-31 |
| IT7949451A0 (it) | 1979-06-18 |
| BG15574A3 (bg) | 1972-05-20 |
| BR6911739D0 (pt) | 1973-05-31 |
| IE33269B1 (en) | 1974-05-01 |
| SE352638B (is") | 1973-01-08 |
| PL69767B1 (en) | 1973-08-31 |
| RO56172A (is") | 1974-09-01 |
| CS163742B2 (is") | 1975-11-07 |
| BE737748A (is") | 1970-02-20 |
| US3660380A (en) | 1972-05-02 |
| ES370394A1 (es) | 1971-04-16 |
| IL32853A0 (en) | 1969-11-12 |
| GB1277132A (en) | 1972-06-07 |
| AT289127B (de) | 1971-04-13 |
| NO124073B (is") | 1972-02-28 |
| NL6912652A (is") | 1970-02-24 |
| FR2016009A1 (is") | 1970-04-30 |
| IE33269L (en) | 1970-02-20 |
| US3743734A (en) | 1973-07-03 |
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