NO135982B - - Google Patents
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- Publication number
- NO135982B NO135982B NO4848/71A NO484871A NO135982B NO 135982 B NO135982 B NO 135982B NO 4848/71 A NO4848/71 A NO 4848/71A NO 484871 A NO484871 A NO 484871A NO 135982 B NO135982 B NO 135982B
- Authority
- NO
- Norway
- Prior art keywords
- cyclopropane
- carboxylic acid
- diphenyl
- piperidine
- ring
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- YITOQLBHYDWJBQ-UHFFFAOYSA-N 2,2-diphenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1(C=1C=CC=CC=1)C1=CC=CC=C1 YITOQLBHYDWJBQ-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- -1 alkoxy radical Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- WAVYMOJAHLGDCA-UHFFFAOYSA-N 2,2-diphenylcyclopropane-1-carbonyl chloride Chemical compound ClC(=O)C1CC1(C=1C=CC=CC=1)C1=CC=CC=C1 WAVYMOJAHLGDCA-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229960003750 ethyl chloride Drugs 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 206010011224 Cough Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 230000000954 anitussive effect Effects 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
- 238000002474 experimental method Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 2
- 241000699670 Mus sp. Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 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
- 210000005036 nerve Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 1
- KVWBFWPNINUDOX-UHFFFAOYSA-N 2-(diethylamino)ethyl 2,2-diphenylcyclopropane-1-carboxylate Chemical compound CCN(CC)CCOC(=O)C1CC1(C=1C=CC=CC=1)C1=CC=CC=C1 KVWBFWPNINUDOX-UHFFFAOYSA-N 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 208000019300 CLIPPERS Diseases 0.000 description 1
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 1
- 101100129922 Caenorhabditis elegans pig-1 gene Proteins 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 101100520057 Drosophila melanogaster Pig1 gene Proteins 0.000 description 1
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 208000021930 chronic lymphocytic inflammation with pontine perivascular enhancement responsive to steroids Diseases 0.000 description 1
- 229960004415 codeine phosphate Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 210000003801 laryngeal nerve Anatomy 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 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
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910052700 potassium Chemical class 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 238000000718 qrs complex Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6202470A GB1363640A (en) | 1970-12-31 | 1970-12-31 | Esters of 2,2-diphenyl - cyclopropane - carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135982B true NO135982B (ja) | 1977-03-28 |
| NO135982C NO135982C (ja) | 1977-07-06 |
Family
ID=10487788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4848/71A NO135982C (ja) | 1970-12-31 | 1971-12-27 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3846436A (ja) |
| JP (1) | JPS541700B1 (ja) |
| AT (1) | AT315141B (ja) |
| AU (1) | AU3741071A (ja) |
| BE (1) | BE777347A (ja) |
| CH (1) | CH537362A (ja) |
| DE (1) | DE2164988C3 (ja) |
| DK (1) | DK134155B (ja) |
| ES (1) | ES398495A1 (ja) |
| FR (1) | FR2120035B1 (ja) |
| GB (1) | GB1363640A (ja) |
| NL (1) | NL177491C (ja) |
| NO (1) | NO135982C (ja) |
| SE (1) | SE380793B (ja) |
| ZA (1) | ZA718629B (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS604170B2 (ja) * | 1974-03-29 | 1985-02-01 | 大日本製薬株式会社 | １，２− ジフエニルエタノ−ルアミン誘導体の製法 |
| DE3735712A1 (de) * | 1987-10-22 | 1989-05-03 | Robert Wolff | Schraubstock |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1313850A (fr) * | 1961-11-09 | 1963-01-04 | Rolland Lab A | Nouveau procédé pour la préparation d'aminoesters dérivés de l'acide propionique |
| US3317526A (en) * | 1964-07-16 | 1967-05-02 | Astra Ab | Omega-tertiaryamino butynol-1-phenylcycloalkane carboxylates |
-
1970
- 1970-12-31 GB GB6202470A patent/GB1363640A/en not_active Expired
-
1971
- 1971-12-24 AU AU37410/71A patent/AU3741071A/en not_active Expired
- 1971-12-27 FR FR7146813A patent/FR2120035B1/fr not_active Expired
- 1971-12-27 CH CH1897171A patent/CH537362A/fr not_active IP Right Cessation
- 1971-12-27 NO NO4848/71A patent/NO135982C/no unknown
- 1971-12-28 ZA ZA718629A patent/ZA718629B/xx unknown
- 1971-12-28 BE BE777347A patent/BE777347A/xx not_active IP Right Cessation
- 1971-12-28 DE DE2164988A patent/DE2164988C3/de not_active Expired
- 1971-12-28 JP JP398672A patent/JPS541700B1/ja active Pending
- 1971-12-29 SE SE7116817A patent/SE380793B/xx unknown
- 1971-12-30 ES ES398495A patent/ES398495A1/es not_active Expired
- 1971-12-30 AT AT1125171A patent/AT315141B/de not_active IP Right Cessation
- 1971-12-30 NL NLAANVRAGE7118162,A patent/NL177491C/xx not_active IP Right Cessation
- 1971-12-30 US US00214473A patent/US3846436A/en not_active Expired - Lifetime
- 1971-12-30 DK DK645671AA patent/DK134155B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT315141B (de) | 1974-05-10 |
| NL7118162A (ja) | 1972-07-04 |
| DK134155B (da) | 1976-09-20 |
| SE380793B (sv) | 1975-11-17 |
| JPS541700B1 (ja) | 1979-01-27 |
| DE2164988C3 (de) | 1982-01-14 |
| CH537362A (fr) | 1973-05-31 |
| BE777347A (fr) | 1972-04-17 |
| AU3741071A (en) | 1973-06-28 |
| AU465421B2 (ja) | 1975-09-25 |
| ES398495A1 (es) | 1974-08-01 |
| NO135982C (ja) | 1977-07-06 |
| GB1363640A (en) | 1974-08-14 |
| DE2164988B2 (de) | 1981-03-12 |
| DK134155C (ja) | 1977-02-21 |
| FR2120035A1 (ja) | 1972-08-11 |
| US3846436A (en) | 1974-11-05 |
| NL177491C (nl) | 1985-10-01 |
| DE2164988A1 (de) | 1972-07-20 |
| ZA718629B (en) | 1972-10-25 |
| FR2120035B1 (ja) | 1974-11-15 |
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