NO134295B - - Google Patents
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- Publication number
- NO134295B NO134295B NO723628A NO362872A NO134295B NO 134295 B NO134295 B NO 134295B NO 723628 A NO723628 A NO 723628A NO 362872 A NO362872 A NO 362872A NO 134295 B NO134295 B NO 134295B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- reacted
- naphthol
- tetrahydro
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 48
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 7
- 201000004792 malaria Diseases 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- -1 nitrogen-containing heterocyclic compounds Chemical class 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- WBDXZEVJTHUDGI-UHFFFAOYSA-N 4-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CN(CC)CC)=CC(NC=3C4=CC=C(Cl)C=C4N=CC=3)=C21 WBDXZEVJTHUDGI-UHFFFAOYSA-N 0.000 description 4
- 239000003430 antimalarial agent Substances 0.000 description 4
- 244000045947 parasite Species 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
- 230000000078 anti-malarial effect Effects 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- HMFNMPMFPLADJH-UHFFFAOYSA-N 4-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-(diethylaminomethyl)-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1CCCC2=C(O)C(CN(CC)CC)=CC(NC=3C4=CC(OC)=CC=C4N=C4C=C(Cl)C=CC4=3)=C21 HMFNMPMFPLADJH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229930192627 Naphthoquinone Natural products 0.000 description 2
- 208000009182 Parasitemia Diseases 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- UCZOSSVIJDUQAT-UHFFFAOYSA-N n-(4-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide Chemical compound C1CCCC2=C1C(O)=CC=C2NC(=O)C UCZOSSVIJDUQAT-UHFFFAOYSA-N 0.000 description 2
- ARPLEZKERSOKCB-UHFFFAOYSA-N n-[3-(diethylaminomethyl)-4-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1CCCC2=C(O)C(CN(CC)CC)=CC(NC(C)=O)=C21 ARPLEZKERSOKCB-UHFFFAOYSA-N 0.000 description 2
- 150000002791 naphthoquinones Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RVMDQSIRTSDBRH-UHFFFAOYSA-N 2-(diethylaminomethyl)-4-nitronaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CN(CC)CC)=CC([N+]([O-])=O)=C21 RVMDQSIRTSDBRH-UHFFFAOYSA-N 0.000 description 1
- IMPSXANDTQSLMH-UHFFFAOYSA-N 4-amino-2-(diethylaminomethyl)naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CN(CC)CC)=CC(N)=C21 IMPSXANDTQSLMH-UHFFFAOYSA-N 0.000 description 1
- XYMPDDSYKFZFMR-UHFFFAOYSA-N 4-amino-3-methyl-2-piperidin-1-yl-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound CC1=C(N)C=2CCCCC=2C(O)=C1N1CCCCC1 XYMPDDSYKFZFMR-UHFFFAOYSA-N 0.000 description 1
- OKGJUCMRAGHHTB-UHFFFAOYSA-N 4-amino-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1CCCC2=C1C(O)=CC=C2N OKGJUCMRAGHHTB-UHFFFAOYSA-N 0.000 description 1
- AUIRNGLMBHIITH-UHFFFAOYSA-N 4-nitronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C([N+]([O-])=O)C2=C1 AUIRNGLMBHIITH-UHFFFAOYSA-N 0.000 description 1
- RYRNQWYNHLLOGX-UHFFFAOYSA-N 6,9-dichloro-2-methoxyacridine Chemical compound C1=C(Cl)C=CC2=C(Cl)C3=CC(OC)=CC=C3N=C21 RYRNQWYNHLLOGX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000224017 Plasmodium berghei Species 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical compound [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229960001444 amodiaquine Drugs 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000004159 blood analysis Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 230000001545 erythrolytic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000000973 gametocyte Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- KQINBKPGRHVPFD-UHFFFAOYSA-N n-[4-hydroxy-3-(piperidin-1-ylmethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]acetamide Chemical compound OC=1C=2CCCCC=2C(NC(=O)C)=CC=1CN1CCCCC1 KQINBKPGRHVPFD-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/06—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen 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
- C07D227/10—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D215/40—Nitrogen atoms attached in position 8
-
- 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
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7113236A SE375991B (de) | 1971-10-19 | 1971-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO134295B true NO134295B (de) | 1976-06-08 |
Family
ID=20297073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO723628A NO134295B (de) | 1971-10-19 | 1972-10-10 |
Country Status (12)
| Country | Link |
|---|---|
| AT (2) | AT320653B (de) |
| AU (1) | AU4779972A (de) |
| BE (1) | BE789971A (de) |
| DE (1) | DE2250164A1 (de) |
| DK (1) | DK132889B (de) |
| FI (1) | FI51100B (de) |
| FR (1) | FR2157884B1 (de) |
| GB (1) | GB1365031A (de) |
| NL (1) | NL7214146A (de) |
| NO (1) | NO134295B (de) |
| SE (1) | SE375991B (de) |
| ZA (1) | ZA727263B (de) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB612115A (en) * | 1945-10-23 | 1948-11-09 | Parke Davis & Co | Process for the manufacture of quinoline compounds |
| GB603533A (en) * | 1945-10-23 | 1948-06-17 | Parke Davis & Co | Process for the manufacture of acridine compounds |
-
0
- BE BE789971D patent/BE789971A/xx unknown
-
1971
- 1971-10-19 SE SE7113236A patent/SE375991B/xx unknown
-
1972
- 1972-10-10 NO NO723628A patent/NO134295B/no unknown
- 1972-10-11 ZA ZA727263A patent/ZA727263B/xx unknown
- 1972-10-13 DE DE2250164A patent/DE2250164A1/de active Pending
- 1972-10-16 AU AU47799/72A patent/AU4779972A/en not_active Expired
- 1972-10-17 DK DK511572AA patent/DK132889B/da unknown
- 1972-10-17 GB GB4782572A patent/GB1365031A/en not_active Expired
- 1972-10-18 AT AT890872A patent/AT320653B/de not_active IP Right Cessation
- 1972-10-18 AT AT112674*1A patent/AT325049B/de not_active IP Right Cessation
- 1972-10-18 FR FR7236970A patent/FR2157884B1/fr not_active Expired
- 1972-10-18 FI FI2881/72A patent/FI51100B/fi active
- 1972-10-19 NL NL7214146A patent/NL7214146A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2157884B1 (de) | 1976-09-17 |
| SE375991B (de) | 1975-05-05 |
| GB1365031A (en) | 1974-08-29 |
| BE789971A (fr) | 1973-04-12 |
| DE2250164A1 (de) | 1973-05-17 |
| FR2157884A1 (de) | 1973-06-08 |
| AT325049B (de) | 1975-09-25 |
| NL7214146A (de) | 1973-04-25 |
| DK132889B (da) | 1976-02-23 |
| AT320653B (de) | 1975-02-25 |
| FI51100B (de) | 1976-06-30 |
| ZA727263B (en) | 1973-06-27 |
| AU4779972A (en) | 1974-04-26 |
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