DK142173B - Analogifremgangsmåde til fremstilling af acetamidinderivater eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af acetamidinderivater eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK142173B DK142173B DK302373AA DK302373A DK142173B DK 142173 B DK142173 B DK 142173B DK 302373A A DK302373A A DK 302373AA DK 302373 A DK302373 A DK 302373A DK 142173 B DK142173 B DK 142173B
- Authority
- DK
- Denmark
- Prior art keywords
- benzodioxan
- acetamidine
- pentamethylene
- aza
- compound
- Prior art date
Links
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical class CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 title description 11
- 239000002253 acid Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 37
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 23
- 229940126062 Compound A Drugs 0.000 description 19
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 19
- 230000001684 chronic effect Effects 0.000 description 17
- 206010020772 Hypertension Diseases 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 230000001154 acute effect Effects 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 9
- 239000002220 antihypertensive agent Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 229940030600 antihypertensive agent Drugs 0.000 description 7
- 230000004872 arterial blood pressure Effects 0.000 description 7
- -1 methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-hydroxyethylamino, 2-hydroxy-n-propylamino, carbethoxyamino, phenylamino, chlorophenylamino, fluorophenylamino Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 210000003734 kidney Anatomy 0.000 description 5
- 230000004899 motility Effects 0.000 description 5
- 230000001624 sedative effect Effects 0.000 description 5
- 230000002908 adrenolytic effect Effects 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000003098 Ganglion Cysts Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000001089 Multiple system atrophy Diseases 0.000 description 2
- 206010031127 Orthostatic hypotension Diseases 0.000 description 2
- 208000005400 Synovial Cyst Diseases 0.000 description 2
- 210000004100 adrenal gland Anatomy 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 210000003516 pericardium Anatomy 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- QLEIDMAURCRVCX-UHFFFAOYSA-N 1-propylpiperazine Chemical compound CCCN1CCNCC1 QLEIDMAURCRVCX-UHFFFAOYSA-N 0.000 description 1
- PWZFEIJALHLRKF-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-3-yl)acetonitrile Chemical compound C1=CC=C2OC(CC#N)COC2=C1 PWZFEIJALHLRKF-UHFFFAOYSA-N 0.000 description 1
- VWZUIIYOJGQRBR-UHFFFAOYSA-N 2-(3,4-dihydroxyanilino)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC1=CC=C(O)C(O)=C1 VWZUIIYOJGQRBR-UHFFFAOYSA-N 0.000 description 1
- ZJJIGZSWNQSAPS-UHFFFAOYSA-N 3-ethyl-2,3-dihydro-1,4-benzodioxine Chemical compound C1=CC=C2OC(CC)COC2=C1 ZJJIGZSWNQSAPS-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010016807 Fluid retention Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical class C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 1
- 208000029422 Hypernatremia Diseases 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
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- 206010028735 Nasal congestion Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 239000002568 adrenergic antihypertensivea Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 230000001466 anti-adreneric effect Effects 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 230000009989 contractile response Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002638 denervation Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000000609 ganglia Anatomy 0.000 description 1
- 230000000574 ganglionic effect Effects 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000004873 systolic arterial blood pressure Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 210000001065 vasomotor system Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2569772A GB1382602A (en) | 1972-06-01 | 1972-06-01 | Benzodioxan compounds and process for preparing the same |
| GB2569772 | 1972-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142173B true DK142173B (da) | 1980-09-15 |
| DK142173C DK142173C (xx) | 1981-08-24 |
Family
ID=10231839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK302373AA DK142173B (da) | 1972-06-01 | 1973-05-30 | Analogifremgangsmåde til fremstilling af acetamidinderivater eller syreadditionssalte deraf. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3891648A (xx) |
| JP (1) | JPS4942682A (xx) |
| AR (1) | AR197137A1 (xx) |
| AT (1) | AT325042B (xx) |
| AU (1) | AU468544B2 (xx) |
| BE (1) | BE799718A (xx) |
| CA (1) | CA1003834A (xx) |
| CH (1) | CH572052A5 (xx) |
| DE (1) | DE2328061A1 (xx) |
| DK (1) | DK142173B (xx) |
| ES (1) | ES415267A1 (xx) |
| FI (1) | FI55339C (xx) |
| FR (1) | FR2186254B1 (xx) |
| GB (1) | GB1382602A (xx) |
| HU (1) | HU165378B (xx) |
| IE (1) | IE37579B1 (xx) |
| IN (1) | IN139164B (xx) |
| NL (1) | NL7307108A (xx) |
| NO (1) | NO137693C (xx) |
| OA (1) | OA04416A (xx) |
| SE (1) | SE396078B (xx) |
| SU (1) | SU468413A3 (xx) |
| YU (1) | YU35020B (xx) |
| ZA (1) | ZA732909B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806663A (en) * | 1987-04-06 | 1989-02-21 | The University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4851554A (en) * | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4831156A (en) * | 1987-09-30 | 1989-05-16 | The University Of Tennessee Research Corp. | 3-substituted 2-alkyl indole derivatives |
| US5427068A (en) * | 1992-09-04 | 1995-06-27 | Spread Spectrum | Rotary compressor and engine machine system |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1315372A (fr) * | 1962-02-14 | 1963-01-18 | Lakeside Lab | Nouveaux dérivés de benzodioxanne et leur préparation |
| US3185692A (en) * | 1962-06-28 | 1965-05-25 | Colgate Palmolive Co | Aminoalkyl-n-benzodioxyl carbamates |
| GB1038333A (en) * | 1963-02-13 | 1966-08-10 | Ici Ltd | Pharmaceutical compositions |
| US3496183A (en) * | 1964-11-19 | 1970-02-17 | Egyt Gyogyszervegyeszeti Gyar | Beta-guanidino-ethyl-piperazine derivatives |
| BE791501A (fr) * | 1971-11-19 | 1973-05-17 | Albert Ag Chem Werke | Diamines cycliques n,n'-disubstituees et leur procede de preparation |
-
1972
- 1972-06-01 GB GB2569772A patent/GB1382602A/en not_active Expired
-
1973
- 1973-04-04 YU YU904/73A patent/YU35020B/xx unknown
- 1973-04-23 AR AR247653A patent/AR197137A1/es active
- 1973-04-27 IE IE671/73A patent/IE37579B1/xx unknown
- 1973-04-30 ZA ZA732909A patent/ZA732909B/xx unknown
- 1973-05-08 CH CH652373A patent/CH572052A5/xx not_active IP Right Cessation
- 1973-05-11 SE SE7306694A patent/SE396078B/xx unknown
- 1973-05-14 US US360142A patent/US3891648A/en not_active Expired - Lifetime
- 1973-05-18 BE BE131261A patent/BE799718A/xx unknown
- 1973-05-22 NL NL7307108A patent/NL7307108A/xx not_active Application Discontinuation
- 1973-05-23 JP JP48058502A patent/JPS4942682A/ja active Pending
- 1973-05-25 FR FR7319050A patent/FR2186254B1/fr not_active Expired
- 1973-05-28 ES ES415267A patent/ES415267A1/es not_active Expired
- 1973-05-28 AU AU56194/73A patent/AU468544B2/en not_active Expired
- 1973-05-28 FI FI1712/73A patent/FI55339C/fi active
- 1973-05-29 IN IN1253/CAL/73A patent/IN139164B/en unknown
- 1973-05-30 DK DK302373AA patent/DK142173B/da not_active IP Right Cessation
- 1973-05-30 NO NO2275/73A patent/NO137693C/no unknown
- 1973-05-30 OA OA54925A patent/OA04416A/xx unknown
- 1973-05-31 SU SU1931801A patent/SU468413A3/ru active
- 1973-05-31 CA CA172,904A patent/CA1003834A/en not_active Expired
- 1973-05-31 HU HULA825A patent/HU165378B/hu unknown
- 1973-06-01 AT AT481573A patent/AT325042B/de not_active IP Right Cessation
- 1973-06-01 DE DE2328061A patent/DE2328061A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ZA732909B (en) | 1974-04-24 |
| SE396078B (sv) | 1977-09-05 |
| SU468413A3 (ru) | 1975-04-25 |
| CA1003834A (en) | 1977-01-18 |
| JPS4942682A (xx) | 1974-04-22 |
| YU90473A (en) | 1979-12-31 |
| DK142173C (xx) | 1981-08-24 |
| IE37579B1 (en) | 1977-08-31 |
| US3891648A (en) | 1975-06-24 |
| BE799718A (fr) | 1973-11-19 |
| AT325042B (de) | 1975-09-25 |
| ES415267A1 (es) | 1976-02-01 |
| CH572052A5 (xx) | 1976-01-30 |
| NL7307108A (xx) | 1973-12-04 |
| AU5619473A (en) | 1974-11-28 |
| DE2328061A1 (de) | 1973-12-13 |
| NO137693C (no) | 1978-04-05 |
| FI55339B (fi) | 1979-03-30 |
| YU35020B (en) | 1980-06-30 |
| FI55339C (fi) | 1979-07-10 |
| IN139164B (xx) | 1976-05-15 |
| NO137693B (no) | 1977-12-27 |
| OA04416A (fr) | 1980-02-29 |
| IE37579L (en) | 1973-12-01 |
| AU468544B2 (en) | 1976-01-15 |
| AR197137A1 (es) | 1974-03-15 |
| GB1382602A (en) | 1975-02-05 |
| FR2186254A1 (xx) | 1974-01-11 |
| FR2186254B1 (xx) | 1977-04-08 |
| HU165378B (xx) | 1974-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |