CA1065324A - 2-aminoalkyl-3,3a,4,5,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2h-indazoles and related cyclohepta (c) pyrazoles and cyclopentapyrazoles - Google Patents
2-aminoalkyl-3,3a,4,5,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2h-indazoles and related cyclohepta (c) pyrazoles and cyclopentapyrazolesInfo
- Publication number
- CA1065324A CA1065324A CA226,132A CA226132A CA1065324A CA 1065324 A CA1065324 A CA 1065324A CA 226132 A CA226132 A CA 226132A CA 1065324 A CA1065324 A CA 1065324A
- Authority
- CA
- Canada
- Prior art keywords
- phenylmethylene
- compound
- phenyl
- hexahydro
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- UREWVVFRSGFOEL-UHFFFAOYSA-N cyclohepta[c]pyrazole Chemical class C1=CC=CC=C2C=NN=C21 UREWVVFRSGFOEL-UHFFFAOYSA-N 0.000 title 1
- PZAYJNNTMOGLPX-UHFFFAOYSA-N cyclopenta[c]pyrazole Chemical class N1=NC2=CC=CC2=C1 PZAYJNNTMOGLPX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 33
- -1 hydrazine compound Chemical class 0.000 claims description 29
- 150000003891 oxalate salts Chemical class 0.000 claims description 25
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 17
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 7
- CTKKGXDAWIAYSA-UHFFFAOYSA-N 2,6-dibenzylidenecyclohexan-1-one Chemical compound O=C1C(=CC=2C=CC=CC=2)CCCC1=CC1=CC=CC=C1 CTKKGXDAWIAYSA-UHFFFAOYSA-N 0.000 claims description 6
- WTVHNPWCSPBZFF-UHFFFAOYSA-N 3-(8-benzylidene-3-phenyl-3,3a,4,5,6,7-hexahydrocyclohepta[c]pyrazol-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C=1C=CC=CC=1C1N(CCCN(C)C)N=C2C1CCCCC2=CC1=CC=CC=C1 WTVHNPWCSPBZFF-UHFFFAOYSA-N 0.000 claims description 6
- YUTKWFIHTBVNIE-UHFFFAOYSA-N 3-hydrazinyl-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCNN YUTKWFIHTBVNIE-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- ZHJNAQNCUSKTRA-UHFFFAOYSA-N 3-(7-benzylidene-3-phenyl-3a,4,5,6-tetrahydro-3h-indazol-2-yl)-n,n-diethylpropan-1-amine Chemical compound C=1C=CC=CC=1C1N(CCCN(CC)CC)N=C2C1CCCC2=CC1=CC=CC=C1 ZHJNAQNCUSKTRA-UHFFFAOYSA-N 0.000 claims description 3
- QPYNETAIAKXHTF-UHFFFAOYSA-N 3-(7-benzylidene-3-phenyl-3a,4,5,6-tetrahydro-3h-indazol-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C=1C=CC=CC=1C1N(CCCN(C)C)N=C2C1CCCC2=CC1=CC=CC=C1 QPYNETAIAKXHTF-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- CDWCNIVDIALVDN-UHFFFAOYSA-N 2,7-dibenzylidenecycloheptan-1-one Chemical compound O=C1C(=CC=2C=CC=CC=2)CCCCC1=CC1=CC=CC=C1 CDWCNIVDIALVDN-UHFFFAOYSA-N 0.000 claims description 2
- XXYDEJAJDOABCE-UHFFFAOYSA-N 2-hydrazinyl-n,n-dimethylethanamine Chemical compound CN(C)CCNN XXYDEJAJDOABCE-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 4
- NNPZGRUMFLDSMT-UHFFFAOYSA-N 2-(7-benzylidene-3-phenyl-3a,4,5,6-tetrahydro-3h-indazol-2-yl)-n,n-dimethylethanamine Chemical compound C=1C=CC=CC=1C1N(CCN(C)C)N=C2C1CCCC2=CC1=CC=CC=C1 NNPZGRUMFLDSMT-UHFFFAOYSA-N 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- CVTOCKKPVXJIJK-UHFFFAOYSA-N 2,5-dibenzylidenecyclopentan-1-one Chemical compound O=C1C(=CC=2C=CC=CC=2)CCC1=CC1=CC=CC=C1 CVTOCKKPVXJIJK-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical group 0.000 abstract description 5
- 150000001204 N-oxides Chemical group 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 239000003874 central nervous system depressant Substances 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- WGZYVHFXLPDNDL-UHFFFAOYSA-N 4-benzoyl-2-phenylpyrazole-3-carbonitrile Chemical compound C=1C=CC=CC=1C(=O)C(=C1C#N)C=NN1C1=CC=CC=C1 WGZYVHFXLPDNDL-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 102100037327 Chondrolectin Human genes 0.000 description 3
- 101000879734 Homo sapiens Chondrolectin Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000003935 benzaldehydes Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 241000700159 Rattus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 150000002689 maleic acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- KMWHQYDMBYABKL-UHFFFAOYSA-N 1-iodohexadecane Chemical compound CCCCCCCCCCCCCCCCI KMWHQYDMBYABKL-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ITPNKJOIQUOQPN-UHFFFAOYSA-N 2-indazol-2-ylethanamine Chemical compound C1=CC=CC2=NN(CCN)C=C21 ITPNKJOIQUOQPN-UHFFFAOYSA-N 0.000 description 1
- YXWOYHGDGSGAGA-UHFFFAOYSA-N 3-(7-benzylidene-5-methyl-3-phenyl-3a,4,5,6-tetrahydro-3h-indazol-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1C(C)CC2C(C=3C=CC=CC=3)N(CCCN(C)C)N=C2C1=CC1=CC=CC=C1 YXWOYHGDGSGAGA-UHFFFAOYSA-N 0.000 description 1
- IEVRHAUJJJBXFH-UHFFFAOYSA-N 3-ethylcyclohexan-1-one Chemical compound CCC1CCCC(=O)C1 IEVRHAUJJJBXFH-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- MAUCRURSQMOFGV-UHFFFAOYSA-N 4-propylbenzaldehyde Chemical compound CCCC1=CC=C(C=O)C=C1 MAUCRURSQMOFGV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical class O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical group O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- JKAPLXAKEPFZOG-UHFFFAOYSA-N n,n-diethyl-3-hydrazinylpropan-1-amine Chemical group CCN(CC)CCCNN JKAPLXAKEPFZOG-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46917174A | 1974-05-13 | 1974-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1065324A true CA1065324A (en) | 1979-10-30 |
Family
ID=23862720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,132A Expired CA1065324A (en) | 1974-05-13 | 1975-05-02 | 2-aminoalkyl-3,3a,4,5,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2h-indazoles and related cyclohepta (c) pyrazoles and cyclopentapyrazoles |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS50160271A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1065324A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2521299A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2270871B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1512653A (cg-RX-API-DMAC10.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4004007A (en) * | 1975-08-08 | 1977-01-18 | E. R. Squibb & Sons, Inc. | 2-Heterocyclicalkyl-3,3a,4,5,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2H-indazoles |
| ID17907A (id) * | 1997-02-20 | 1998-02-05 | Fakultas Farmasi Uni Gajah Mad | Turunan benzilidin sikloheksanon benzilidin siklopentanon binzilidin aseton dan pembuatannya |
| CN101809016A (zh) * | 2007-06-01 | 2010-08-18 | 先灵公司 | γ-分泌酶调节剂 |
| AU2009314205A1 (en) * | 2008-11-13 | 2010-05-20 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
-
1975
- 1975-05-02 CA CA226,132A patent/CA1065324A/en not_active Expired
- 1975-05-09 GB GB1968275A patent/GB1512653A/en not_active Expired
- 1975-05-13 FR FR7514896A patent/FR2270871B1/fr not_active Expired
- 1975-05-13 DE DE19752521299 patent/DE2521299A1/de not_active Ceased
- 1975-05-13 JP JP5788275A patent/JPS50160271A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1512653A (en) | 1978-06-01 |
| JPS50160271A (cg-RX-API-DMAC10.html) | 1975-12-25 |
| DE2521299A1 (de) | 1975-11-27 |
| FR2270871B1 (cg-RX-API-DMAC10.html) | 1978-08-04 |
| FR2270871A1 (cg-RX-API-DMAC10.html) | 1975-12-12 |
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