NO135984B - - Google Patents
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- Publication number
- NO135984B NO135984B NO2521/72A NO252172A NO135984B NO 135984 B NO135984 B NO 135984B NO 2521/72 A NO2521/72 A NO 2521/72A NO 252172 A NO252172 A NO 252172A NO 135984 B NO135984 B NO 135984B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- cyclopropyl
- alcohol
- phenoxy
- formula
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000010992 reflux Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- -1 e.g. ethanol Chemical compound 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- VKTBILBRBSALKI-UHFFFAOYSA-N 2-cyclopropylphenol Chemical compound OC1=CC=CC=C1C1CC1 VKTBILBRBSALKI-UHFFFAOYSA-N 0.000 claims description 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 4
- YFBPRBZDQSMTKG-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dihydroimidazole Chemical compound ClCC1=NCCN1 YFBPRBZDQSMTKG-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- JBYVNJSQTCGHEU-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-ylmethanol Chemical compound OCC1=NCCN1 JBYVNJSQTCGHEU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 description 4
- MEPBPBVEALFFOB-UHFFFAOYSA-N 2-(2-cyclopropylphenoxy)acetonitrile Chemical compound C1(CC1)C1=C(OCC#N)C=CC=C1 MEPBPBVEALFFOB-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- 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 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 206010039083 rhinitis Diseases 0.000 description 4
- 239000005526 vasoconstrictor agent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DVKIMTJCOGJSKG-UHFFFAOYSA-N 2-(2-cyclopropylphenoxy)acetic acid Chemical compound C1(CC1)C1=C(OCC(=O)O)C=CC=C1 DVKIMTJCOGJSKG-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229960004970 fenoxazoline Drugs 0.000 description 2
- GFYSWQDCHLWRMQ-UHFFFAOYSA-N fenoxazoline Chemical compound CC(C)C1=CC=CC=C1OCC1=NCCN1 GFYSWQDCHLWRMQ-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 201000009240 nasopharyngitis Diseases 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000000689 upper leg Anatomy 0.000 description 2
- GBVGHNOPZHPBKZ-UHFFFAOYSA-N 1-naphthalen-2-yl-4,5-dihydroimidazole Chemical compound C1=C(C=CC2=CC=CC=C12)N1C=NCC1 GBVGHNOPZHPBKZ-UHFFFAOYSA-N 0.000 description 1
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical class C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 description 1
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 1
- 235000004480 Bombax malabaricum Nutrition 0.000 description 1
- 244000293889 Bombax malabaricum Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- 206010028735 Nasal congestion Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 208000036071 Rhinorrhea Diseases 0.000 description 1
- 206010039101 Rhinorrhoea Diseases 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 201000009151 chronic rhinitis Diseases 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- PIQVDUKEQYOJNR-VZXSFKIWSA-N cocaine hydrochloride Chemical compound [Cl-].O([C@H]1C[C@@H]2CC[C@@H]([NH+]2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 PIQVDUKEQYOJNR-VZXSFKIWSA-N 0.000 description 1
- 229960003771 cocaine hydrochloride Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960005016 naphazoline Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7125858A FR2145423B1 (OSRAM) | 1971-07-15 | 1971-07-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135984B true NO135984B (OSRAM) | 1977-03-28 |
| NO135984C NO135984C (OSRAM) | 1977-07-06 |
Family
ID=9080387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2521/72A NO135984C (OSRAM) | 1971-07-15 | 1972-07-13 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3803130A (OSRAM) |
| JP (1) | JPS5038110B1 (OSRAM) |
| AU (1) | AU475371B2 (OSRAM) |
| BE (1) | BE786263A (OSRAM) |
| CA (1) | CA978534A (OSRAM) |
| DE (1) | DE2234714C3 (OSRAM) |
| DK (1) | DK128927B (OSRAM) |
| ES (1) | ES404927A1 (OSRAM) |
| FR (1) | FR2145423B1 (OSRAM) |
| GB (1) | GB1386355A (OSRAM) |
| LU (1) | LU65723A1 (OSRAM) |
| NL (1) | NL148051B (OSRAM) |
| NO (1) | NO135984C (OSRAM) |
| SE (1) | SE393109B (OSRAM) |
| ZA (1) | ZA724878B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2485006A1 (fr) * | 1980-06-19 | 1981-12-24 | Synthelabo | Derives d'amidoximes, leur preparation et leur application en therapeutique |
-
1971
- 1971-07-15 FR FR7125858A patent/FR2145423B1/fr not_active Expired
-
1972
- 1972-07-13 NO NO2521/72A patent/NO135984C/no unknown
- 1972-07-13 SE SE7209248A patent/SE393109B/xx unknown
- 1972-07-13 BE BE786263A patent/BE786263A/xx not_active IP Right Cessation
- 1972-07-13 DK DK351272AA patent/DK128927B/da not_active IP Right Cessation
- 1972-07-14 CA CA147,133A patent/CA978534A/en not_active Expired
- 1972-07-14 DE DE2234714A patent/DE2234714C3/de not_active Expired
- 1972-07-14 NL NL727209788A patent/NL148051B/xx not_active IP Right Cessation
- 1972-07-14 ZA ZA724878A patent/ZA724878B/xx unknown
- 1972-07-14 GB GB3313572A patent/GB1386355A/en not_active Expired
- 1972-07-14 LU LU65723D patent/LU65723A1/xx unknown
- 1972-07-15 JP JP47071214A patent/JPS5038110B1/ja active Pending
- 1972-07-15 ES ES404927A patent/ES404927A1/es not_active Expired
- 1972-07-17 US US00272142A patent/US3803130A/en not_active Expired - Lifetime
- 1972-07-17 AU AU44645/72A patent/AU475371B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE393109B (sv) | 1977-05-02 |
| DE2234714B2 (de) | 1977-09-22 |
| JPS5038110B1 (OSRAM) | 1975-12-06 |
| NO135984C (OSRAM) | 1977-07-06 |
| GB1386355A (en) | 1975-03-05 |
| NL148051B (nl) | 1975-12-15 |
| NL7209788A (OSRAM) | 1973-01-17 |
| FR2145423B1 (OSRAM) | 1974-09-06 |
| ES404927A1 (es) | 1975-06-16 |
| AU475371B2 (en) | 1976-08-19 |
| DE2234714A1 (de) | 1973-02-01 |
| FR2145423A1 (OSRAM) | 1973-02-23 |
| DE2234714C3 (de) | 1978-05-24 |
| LU65723A1 (OSRAM) | 1972-10-30 |
| DK128927B (da) | 1974-07-29 |
| US3803130A (en) | 1974-04-09 |
| BE786263A (fr) | 1972-11-03 |
| AU4464572A (en) | 1974-01-24 |
| ZA724878B (en) | 1973-04-25 |
| CA978534A (en) | 1975-11-25 |
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