NO127670B - - Google Patents
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- Publication number
- NO127670B NO127670B NO04246/68A NO424668A NO127670B NO 127670 B NO127670 B NO 127670B NO 04246/68 A NO04246/68 A NO 04246/68A NO 424668 A NO424668 A NO 424668A NO 127670 B NO127670 B NO 127670B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- given above
- meaning given
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 41
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000001078 anti-cholinergic effect Effects 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- -1 cyclic imine Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000005014 aminoalkynyl group Chemical group 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 14
- 230000002093 peripheral effect Effects 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000001713 cholinergic effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 206010044565 Tremor Diseases 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000002911 mydriatic effect Effects 0.000 description 4
- 229930003347 Atropine Natural products 0.000 description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 230000001022 anti-muscarinic effect Effects 0.000 description 3
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 3
- 229960000396 atropine Drugs 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000812 cholinergic antagonist Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 208000008238 Muscle Spasticity Diseases 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 208000018198 spasticity Diseases 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QWKYDWKEJQCWSI-UHFFFAOYSA-N 1-(5-piperidin-1-ylpent-3-yn-2-yl)pyrrolidin-2-one Chemical compound C1CCC(=O)N1C(C)C#CCN1CCCCC1 QWKYDWKEJQCWSI-UHFFFAOYSA-N 0.000 description 1
- ZLAHHJCKDNOZMP-UHFFFAOYSA-N 1-(5-pyrrolidin-1-ylpent-3-ynyl)pyrrolidin-2-one Chemical compound O=C1CCCN1CCC#CCN1CCCC1 ZLAHHJCKDNOZMP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VYEQRXQPEAJLPZ-UHFFFAOYSA-N 5-pyrrolidin-1-ylpent-3-yn-1-amine Chemical compound NCCC#CCN1CCCC1 VYEQRXQPEAJLPZ-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000006083 Hypokinesia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical compound C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- ZZRMYOZQUCUWFT-UHFFFAOYSA-N but-3-yn-2-amine Chemical compound CC(N)C#C ZZRMYOZQUCUWFT-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000003483 hypokinetic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000001499 parasympathomimetic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 230000010344 pupil dilation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960001032 trihexyphenidyl Drugs 0.000 description 1
Classifications
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51146/67A GB1245743A (en) | 1967-11-09 | 1967-11-09 | Alkynyl lactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127670B true NO127670B (fr) | 1973-07-30 |
Family
ID=10458832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04246/68A NO127670B (fr) | 1967-11-09 | 1968-10-25 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3925411A (fr) |
| DE (2) | DE1805029A1 (fr) |
| DK (1) | DK131935C (fr) |
| FI (1) | FI49419C (fr) |
| FR (2) | FR8307M (fr) |
| GB (1) | GB1245743A (fr) |
| NL (1) | NL6814854A (fr) |
| NO (1) | NO127670B (fr) |
| SE (1) | SE339225B (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1245743A (en) * | 1967-11-09 | 1971-09-08 | Astra Ab | Alkynyl lactams |
| US4081456A (en) * | 1973-02-28 | 1978-03-28 | Mobil Oil Corporation | Bis-lactam derivatives |
| US5100909A (en) * | 1988-07-25 | 1992-03-31 | The Upjohn Company | Acetylenic imidazoles having central nervous system activity |
| AU620894B2 (en) * | 1988-07-25 | 1992-02-27 | Upjohn Company, The | Acetylenic imidazoles having central nervous system activity |
| US5225567A (en) * | 1988-10-27 | 1993-07-06 | The Upjohn Company | Heterocyclic acetylenic amines having central nervous system activity |
| US5157124A (en) * | 1988-10-27 | 1992-10-20 | The Upjohn Company | Heterocyclic acetylenic amines having central nervous system activity |
| US5137905A (en) * | 1988-10-27 | 1992-08-11 | The Upjohn Company | Heterocyclic acetylenic amines having central nervous system activity |
| US4937235A (en) * | 1989-01-23 | 1990-06-26 | American Cyanamid Company | 3- or 4-substituted oxotremorine derivatives |
| IE902294A1 (en) * | 1989-07-06 | 1991-01-16 | Abbott Lab | Alkynyl amines that regulate cholinergic neurotransmission |
| US5837919A (en) * | 1996-12-05 | 1998-11-17 | The United States Of America As Represented By The Secretary Of The Navy | Portable launcher |
| GB201311107D0 (en) * | 2013-06-21 | 2013-08-07 | Univ Edinburgh | Bioorthogonal methods and compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1405319A (fr) * | 1964-05-26 | 1965-07-09 | Ile Auguil Soc Civ | Procédé de préparation de l'(oxo-2 pyrrolidino-1)-1 (pyrrolidino-1)-4 butyne-2, et nouveaux sels de ce composé |
| US3354178A (en) * | 1965-04-09 | 1967-11-21 | Sterling Drug Inc | Nu-(4-amino-2-butynyl)-nu-alkylcarboxamides |
| GB1245743A (en) * | 1967-11-09 | 1971-09-08 | Astra Ab | Alkynyl lactams |
| US3856790A (en) * | 1970-01-06 | 1974-12-24 | American Home Prod | Cyclic amides of 1,4-diaminobut-2-yne |
-
1967
- 1967-11-09 GB GB51146/67A patent/GB1245743A/en not_active Expired
-
1968
- 1968-10-17 NL NL6814854A patent/NL6814854A/xx not_active Application Discontinuation
- 1968-10-24 SE SE14426/68A patent/SE339225B/xx unknown
- 1968-10-25 DE DE19681805029 patent/DE1805029A1/de active Pending
- 1968-10-25 NO NO04246/68A patent/NO127670B/no unknown
- 1968-11-06 DE DE19681807218 patent/DE1807218A1/de active Pending
- 1968-11-07 FR FR172980A patent/FR8307M/fr not_active Expired
- 1968-11-07 FR FR172979A patent/FR1591337A/fr not_active Expired
- 1968-11-08 DK DK542668A patent/DK131935C/da active
- 1968-11-08 FI FI683204A patent/FI49419C/fi active
-
1972
- 1972-11-15 US US306829A patent/US3925411A/en not_active Expired - Lifetime
-
1974
- 1974-05-24 US US05/473,190 patent/US3959311A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE339225B (fr) | 1971-10-04 |
| US3925411A (en) | 1975-12-09 |
| US3959311A (en) | 1976-05-25 |
| DK131935C (da) | 1976-02-23 |
| FR1591337A (fr) | 1970-04-27 |
| FR8307M (fr) | 1970-11-23 |
| USB306829I5 (fr) | 1975-01-28 |
| FI49419B (fr) | 1975-02-28 |
| DK131935B (da) | 1975-09-29 |
| DE1805029A1 (de) | 1969-06-12 |
| NL6814854A (fr) | 1969-05-13 |
| DE1807218A1 (de) | 1969-06-12 |
| GB1245743A (en) | 1971-09-08 |
| FI49419C (fi) | 1975-06-10 |
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