FI57103C - Foerfarande foer framstaellning av antiemetiskt aktiv 5-(1-allyl-2-pyrrolidinylmetylkarbamoyl)-6-metoxi-1h-bensotriazol - Google Patents
Foerfarande foer framstaellning av antiemetiskt aktiv 5-(1-allyl-2-pyrrolidinylmetylkarbamoyl)-6-metoxi-1h-bensotriazol Download PDFInfo
- Publication number
- FI57103C FI57103C FI750525A FI750525A FI57103C FI 57103 C FI57103 C FI 57103C FI 750525 A FI750525 A FI 750525A FI 750525 A FI750525 A FI 750525A FI 57103 C FI57103 C FI 57103C
- Authority
- FI
- Finland
- Prior art keywords
- methoxy
- compound
- acid
- benzotriazole
- allyl
- Prior art date
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- 229910052751 metal Inorganic materials 0.000 title description 2
- 239000002184 metal Substances 0.000 title description 2
- KSEYRUGYKHXGFW-UHFFFAOYSA-N 6-methoxy-N-[(1-prop-2-enyl-2-pyrrolidinyl)methyl]-2H-benzotriazole-5-carboxamide Chemical compound COC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C KSEYRUGYKHXGFW-UHFFFAOYSA-N 0.000 title 1
- 230000004913 activation Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 14
- -1 1H-benzotriazole compound Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- HTGKTSVPJJNEMQ-QMMMGPOBSA-N [(2s)-1-prop-2-enylpyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC=C HTGKTSVPJJNEMQ-QMMMGPOBSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000003474 anti-emetic effect Effects 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 239000002111 antiemetic agent Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 101100256223 Caenorhabditis elegans cho-1 gene Proteins 0.000 claims 1
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- 239000000047 product Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
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- 150000001412 amines Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- XMXQGEHIRILYPP-UHFFFAOYSA-N 5-methoxy-2,3-dihydrobenzotriazole-5-carboxylic acid Chemical compound C(=O)(O)C1(C=CC=2C(NNN=2)=C1)OC XMXQGEHIRILYPP-UHFFFAOYSA-N 0.000 description 4
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- RZAYVTJDINJRRW-UHFFFAOYSA-N 1-acetyl-6-methoxybenzotriazole-5-carbonyl chloride Chemical compound C1=C(C(Cl)=O)C(OC)=CC2=C1N=NN2C(C)=O RZAYVTJDINJRRW-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- ZNWDIENXWNBKIM-UHFFFAOYSA-N methyl 6-methoxy-2h-benzotriazole-5-carboxylate Chemical compound C1=C(OC)C(C(=O)OC)=CC2=NNN=C21 ZNWDIENXWNBKIM-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
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- 231100001274 therapeutic index Toxicity 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical class C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZECQPKLPWGLGMD-UHFFFAOYSA-N 1-amino-6-methoxy-3-nitrocyclohexa-2,4-diene-1-carboxylic acid Chemical compound COC1C(C(=O)O)(C=C(C=C1)[N+](=O)[O-])N ZECQPKLPWGLGMD-UHFFFAOYSA-N 0.000 description 1
- LEGICGXXEKQYBY-UHFFFAOYSA-N 1-amino-6-methoxycyclohexa-2,4-diene-1-carboxylic acid Chemical compound NC1(C(C=CC=C1)OC)C(=O)O LEGICGXXEKQYBY-UHFFFAOYSA-N 0.000 description 1
- ZHPSBMQVLQEIIC-UHFFFAOYSA-N 1-methoxybenzotriazole Chemical compound C1=CC=C2N(OC)N=NC2=C1 ZHPSBMQVLQEIIC-UHFFFAOYSA-N 0.000 description 1
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- AOANPIGDKLHHIC-UHFFFAOYSA-N 4-amino-2-methoxy-5-nitrobenzoic acid Chemical compound COC1=CC(N)=C([N+]([O-])=O)C=C1C(O)=O AOANPIGDKLHHIC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YYGZDSRJEIWEGD-UHFFFAOYSA-N C(C)OC1C(C(=O)OCC)(C=CC=C1)N Chemical compound C(C)OC1C(C(=O)OCC)(C=CC=C1)N YYGZDSRJEIWEGD-UHFFFAOYSA-N 0.000 description 1
- OITQCPIOMXEYAP-UHFFFAOYSA-N COC1C(C(=O)OC)(C=C(C=C1)N)N Chemical compound COC1C(C(=O)OC)(C=C(C=C1)N)N OITQCPIOMXEYAP-UHFFFAOYSA-N 0.000 description 1
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- 229940126062 Compound A Drugs 0.000 description 1
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- YFGQJKBUXPKSAW-ZUDKKNPISA-N [(2r,3r,4s)-6-[(2r,3s,4s)-4-hydroxy-6-[(2r,3s,4s)-4-hydroxy-6-[[(3s,9s,10s,13r,17r)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-3-yl]oxy-2-methyloxan-3-y Chemical compound O([C@H]1[C@@H](OC(C)=O)CC(O[C@@H]1C)O[C@H]1[C@@H](O)CC(O[C@@H]1C)O[C@H]1[C@@H](O)CC(O[C@@H]1C)O[C@@H]1CC2[C@]([C@@H]3C(C4(CC[C@@H]([C@@]4(C)CC3)C=3COC(=O)C=3)O)CC2)(C)CC1)C1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O YFGQJKBUXPKSAW-ZUDKKNPISA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- VMPYTOIPVPQDNX-UHFFFAOYSA-N pyrrolidin-1-ylmethanamine Chemical compound NCN1CCCC1 VMPYTOIPVPQDNX-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Otolaryngology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500919 DE2500919C3 (de) | 1975-01-11 | 5-(l-Allyl-2-pyrrolidinylmethylaminocarbonyl)-6-methoxy-benzotriazol sowie seine pharmazeutisch verträglichen Additionssalze mit Säuren | |
| DE2500919 | 1975-01-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI750525A7 FI750525A7 (enrdf_load_html_response) | 1976-07-12 |
| FI57103B FI57103B (fi) | 1980-02-29 |
| FI57103C true FI57103C (fi) | 1980-06-10 |
Family
ID=5936259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI750525A FI57103C (fi) | 1975-01-11 | 1975-02-25 | Foerfarande foer framstaellning av antiemetiskt aktiv 5-(1-allyl-2-pyrrolidinylmetylkarbamoyl)-6-metoxi-1h-bensotriazol |
Country Status (30)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0794184T3 (da) * | 1994-11-21 | 2001-07-30 | Dainippon Pharmaceutical Co | 6-Methoxy-1H-benzotriazol-5-carboxamidderivater, fremgangsmåde til fremstilling deraf og lægemidler indeholdende dem |
| DE19654038A1 (de) * | 1996-12-23 | 1998-06-25 | Basf Ag | Verfahren zur Herstellung von alpha-Tocopherol oder alpha-Tocopherylacetat durch Umsetzen von Trimethylhydrochinon und Phytol oder Isophytol unter Rückführung des Kondensationskatalysators Zinkchlorid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR6787M (enrdf_load_html_response) * | 1967-08-17 | 1969-03-17 |
-
1975
- 1975-01-31 FR FR7503005A patent/FR2297041A1/fr active Granted
- 1975-02-10 IE IE261/74A patent/IE41349B1/xx unknown
- 1975-02-12 ZA ZA00750903A patent/ZA75903B/xx unknown
- 1975-02-12 IL IL46622A patent/IL46622A/xx unknown
- 1975-02-17 BE BE1006460A patent/BE825605A/xx not_active IP Right Cessation
- 1975-02-24 CY CY975A patent/CY975A/xx unknown
- 1975-02-24 GB GB767475A patent/GB1475234A/en not_active Expired
- 1975-02-25 FI FI750525A patent/FI57103C/fi not_active IP Right Cessation
- 1975-02-25 EG EG94/75A patent/EG11931A/xx active
- 1975-02-26 AR AR257775A patent/AR211237A1/es active
- 1975-02-28 MW MW9/75A patent/MW975A1/xx unknown
- 1975-03-03 SE SE7502343A patent/SE404698B/xx not_active IP Right Cessation
- 1975-03-03 AT AT160475A patent/AT358568B/de not_active IP Right Cessation
- 1975-03-04 ZM ZM28/75A patent/ZM2875A1/xx unknown
- 1975-03-04 YU YU518/75A patent/YU40434B/xx unknown
- 1975-03-04 OA OA55429A patent/OA04965A/xx unknown
- 1975-03-04 CS CS751447A patent/CS219314B2/cs unknown
- 1975-03-07 LU LU72000A patent/LU72000A1/xx unknown
- 1975-03-07 DK DK92375A patent/DK138391C/da active
- 1975-03-07 CA CA221,531A patent/CA1036608A/en not_active Expired
- 1975-03-07 NO NO750759A patent/NO141314C/no unknown
- 1975-03-10 RO RO75100183A patent/RO78909A/ro unknown
- 1975-03-10 JP JP2995475A patent/JPS5616793B2/ja not_active Expired
- 1975-03-10 PL PL1975178625A patent/PL95772B1/pl unknown
- 1975-03-10 NL NL7502831.A patent/NL161985C/xx not_active IP Right Cessation
- 1975-03-10 CH CH300475A patent/CH601290A5/xx not_active IP Right Cessation
- 1975-03-10 RO RO75100181A patent/RO79040A/ro unknown
- 1975-03-10 SU SU7502112074A patent/SU577990A3/ru active
- 1975-03-10 HU HUSO1140A patent/HU170638B/hu unknown
- 1975-03-10 RO RO7581598A patent/RO72712A/ro unknown
- 1975-03-10 DD DD184669A patent/DD117677A5/xx unknown
-
1976
- 1976-09-08 AR AR264621A patent/AR212635A1/es active
-
1978
- 1978-03-16 HK HK141/78A patent/HK14178A/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| MA | Patent expired |
Owner name: SOCIETE D'ETUDES SCIENTIFIQUES ET |