NO314726B1 - Substituerte isokinoliner, anvendelse og fremgangsmåte for fremstilling derav samt farmasöytisk blanding - Google Patents
Substituerte isokinoliner, anvendelse og fremgangsmåte for fremstilling derav samt farmasöytisk blanding Download PDFInfo
- Publication number
- NO314726B1 NO314726B1 NO19994680A NO994680A NO314726B1 NO 314726 B1 NO314726 B1 NO 314726B1 NO 19994680 A NO19994680 A NO 19994680A NO 994680 A NO994680 A NO 994680A NO 314726 B1 NO314726 B1 NO 314726B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- tetrahydro
- trimethoxyphenyl
- propyl
- dimethoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 150000002537 isoquinolines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 41
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 33
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 206010029315 Neuromuscular blockade Diseases 0.000 claims description 3
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- 238000002560 therapeutic procedure Methods 0.000 claims 1
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- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
- 229960003132 halothane Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229960002362 neostigmine Drugs 0.000 description 1
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 229960001412 pentobarbital Drugs 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline 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 nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Surgery (AREA)
- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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GBGB9706117.0A GB9706117D0 (en) | 1997-03-25 | 1997-03-25 | Ultra-short acting neuromuscular blockers |
GBGB9724987.4A GB9724987D0 (en) | 1997-11-27 | 1997-11-27 | Ultra-short acting neuromuscular blockers |
PCT/EP1998/001651 WO1998042674A1 (en) | 1997-03-25 | 1998-03-23 | Substituted isoquinolines as ultra short acting neuromuscular blockers |
Publications (3)
Publication Number | Publication Date |
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NO994680D0 NO994680D0 (no) | 1999-09-24 |
NO994680L NO994680L (no) | 1999-11-24 |
NO314726B1 true NO314726B1 (no) | 2003-05-12 |
Family
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NO19994680A NO314726B1 (no) | 1997-03-25 | 1999-09-24 | Substituerte isokinoliner, anvendelse og fremgangsmåte for fremstilling derav samt farmasöytisk blanding |
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EP (4) | EP1526130A1 (sr) |
JP (3) | JP4112016B2 (sr) |
KR (2) | KR100554601B1 (sr) |
CN (1) | CN1203061C (sr) |
AP (1) | AP1797A (sr) |
AR (1) | AR012156A1 (sr) |
AT (3) | ATE430734T1 (sr) |
AU (2) | AU6730598A (sr) |
BR (1) | BR9808422B1 (sr) |
CA (1) | CA2284802C (sr) |
CO (1) | CO4940499A1 (sr) |
CZ (1) | CZ293786B6 (sr) |
DE (3) | DE69840816D1 (sr) |
DK (2) | DK0971898T3 (sr) |
EA (1) | EA002224B1 (sr) |
EE (1) | EE04113B1 (sr) |
ES (2) | ES2242275T3 (sr) |
HK (1) | HK1023342A1 (sr) |
HR (1) | HRP980157B1 (sr) |
HU (1) | HU228230B1 (sr) |
ID (1) | ID22901A (sr) |
IL (1) | IL131918A (sr) |
IS (2) | IS2346B (sr) |
MA (1) | MA26476A1 (sr) |
MY (1) | MY121316A (sr) |
NO (1) | NO314726B1 (sr) |
NZ (1) | NZ337797A (sr) |
PE (1) | PE68399A1 (sr) |
PL (1) | PL190860B1 (sr) |
PT (2) | PT971898E (sr) |
RS (1) | RS49869B (sr) |
SI (1) | SI0975599T1 (sr) |
TR (1) | TR199902330T2 (sr) |
TW (1) | TW505635B (sr) |
UY (1) | UY24933A1 (sr) |
WO (2) | WO1998042675A1 (sr) |
Families Citing this family (29)
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EA002224B1 (ru) * | 1997-03-25 | 2002-02-28 | Глаксо Груп Лимитед | Замещенные изохинолины в качестве нервно-мышечных блокаторов ультракраткосрочного действия |
US6911455B2 (en) * | 1999-12-22 | 2005-06-28 | Smithkline Beecham Corporation | Methods for preparing pharmaceutical formulations |
US6844904B2 (en) * | 2002-12-07 | 2005-01-18 | Cubic Corporation | Fast PDLC device |
EP1684753A2 (en) * | 2003-10-28 | 2006-08-02 | Cornell Research Foundation, Inc. | Neuromuscular blocking agents and antagonists thereof |
ATE554769T1 (de) * | 2006-12-06 | 2012-05-15 | Cornell Res Foundation Inc | Neuromuskuläre blocker mit mittlerer dauer und antagonisten advon |
WO2008107887A2 (en) * | 2007-03-08 | 2008-09-12 | Chemagis Ltd. | (1r,1'r)-atracurium salts separation process |
BRPI0808581A2 (pt) * | 2007-03-26 | 2014-09-16 | Chemagis Ltd | "método para separar cisatracúrio com alta pureza de uma mistura de isômeros de (1r, 1'r) - atracúrio" |
US8293912B2 (en) * | 2007-05-01 | 2012-10-23 | Chemagis Ltd. | Process for producing cisatracurium compounds and associated intermediates |
US8357807B2 (en) * | 2007-05-01 | 2013-01-22 | Chemagis Ltd. | Isoquinolinium compounds useful in the preparation of cisatracurium and associated intermediates |
BRPI0811687A2 (pt) | 2007-06-18 | 2015-02-18 | Chemagis Ltd | MÉTODO PARA SEPARAR O ISÔMETRO 1R-CIS, 1'R-CIS (cisatracúrio) DE UMA MISTURA DE ISÔMEROS DE SAIS DE (1R, 1'R) - ATRACÚRIO |
EP2176227A1 (en) * | 2007-07-09 | 2010-04-21 | Chemagis Ltd. | Process for producing cisatracurium and associated intermediates |
BRPI0816519A2 (pt) * | 2007-10-29 | 2015-03-24 | Chemagis Ltd | Processo para preparar um sal de r, r'-atracúrio isomericamente enriquecido e sal de r, r'-atracúrio |
BRPI0907656A2 (pt) * | 2008-05-01 | 2019-08-27 | Chemagis Ltd | composto para testar a pureza de cisatracúrio, método para testar a pureza de uma amostra de besilato de cisatracúrio, uso de um composto para testar a pureza de cisatracúrio e processo para preparar compostos para testar a pureza de cisatracúrio |
WO2010107488A1 (en) * | 2009-03-17 | 2010-09-23 | Cornell University | Reversible nondepolarizing neuromuscular blockade agents and methods for their use |
WO2011022491A1 (en) | 2009-08-19 | 2011-02-24 | Cornell University | Cysteine for physiological injection |
JP6236077B2 (ja) * | 2012-06-29 | 2017-11-22 | コーネル・ユニバーシティーCornell University | 持続時間が超短期、短期、または中期の非対称性逆転可能神経筋遮断物質 |
CN103373959A (zh) * | 2013-06-14 | 2013-10-30 | 安徽省先锋制药有限公司 | 顺式苄基异喹啉类化合物的制备方法及其用途 |
WO2014210369A2 (en) * | 2013-06-28 | 2014-12-31 | Cornell University | Reversal of cysteine-inactivated neuromuscular blocking drugs with combinations of reversal agents |
CN108375644B (zh) * | 2016-12-07 | 2021-11-30 | 四川科瑞德制药股份有限公司 | 一种神经肌肉阻滞剂中间体的分析方法 |
CN108938573B (zh) * | 2017-05-26 | 2021-08-10 | 四川科瑞德制药股份有限公司 | 一种神经肌肉阻滞剂组合物及其制备方法和用途 |
CN110776481B (zh) * | 2018-07-24 | 2023-06-16 | 四川大学华西医院 | 一类双阳离子化合物及其制备方法和用途 |
CN109776486A (zh) * | 2019-02-26 | 2019-05-21 | 武汉松石科技股份有限公司 | 一种硫酸亚丙酯的制备方法 |
CN111662230A (zh) * | 2019-03-06 | 2020-09-15 | 四川道珍科技有限公司 | 一类苄基异喹啉化合物、制备方法和用途 |
CN110117297A (zh) * | 2019-04-10 | 2019-08-13 | 珠海市赛纬电子材料股份有限公司 | 一种2-磷酸盐基硫酸丙烯酯的制备方法 |
TW202128628A (zh) * | 2019-12-11 | 2021-08-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 神經肌肉阻滯劑及其製備方法 |
CN111471013B (zh) * | 2020-05-26 | 2021-04-30 | 朗天药业(湖北)有限公司 | 一种米库氯铵及其注射液的制备方法 |
CN111909089B (zh) * | 2020-08-14 | 2023-04-14 | 广东嘉博制药有限公司 | 一种米库氯铵对照品的制备方法 |
CN114057642B (zh) * | 2021-12-10 | 2023-03-28 | 广东嘉博制药有限公司 | 一种米库氯铵中间体的合成方法 |
CN115073373A (zh) * | 2022-07-08 | 2022-09-20 | 广东嘉博制药有限公司 | 一种不对称合成(r)-5’-甲氧基劳丹素的方法 |
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US3004031A (en) | 1958-07-03 | 1961-10-10 | Allen & Hauburys Ltd | Diquaternary salts of papaverino esters |
AU506657B2 (en) * | 1975-12-10 | 1980-01-17 | Wellcome Foundation Limited, The | Isoquinoline derivatives |
DK339078A (da) * | 1977-08-01 | 1979-02-02 | Massachusetts Gen Hospital | Neuromuskulaere blokeringsmidler og fremgangsmaade til deres fremstilling |
US4701460A (en) * | 1980-12-17 | 1987-10-20 | Burroughs Wellcome Co. | Long duration neuromuscular blocking agents |
JPS5899465A (ja) | 1981-11-23 | 1983-06-13 | ザ・ウエルカム・フアウンデ−シヨン・リミテツド | イソキノリン誘導体 |
GB8418303D0 (en) * | 1984-07-18 | 1984-08-22 | Wellcome Found | Compounds |
BG41897A1 (en) * | 1985-07-19 | 1987-09-15 | Ivanov | Dichlormethylate of n, n'- 4, 10- dioxa- 3, 11- bis- tetrahydropapaverine and method for its preparation |
GB9015473D0 (en) | 1990-07-13 | 1990-08-29 | Wellcome Found | Neuromuscular blocking agents |
JPH04112016A (ja) * | 1990-09-03 | 1992-04-14 | Fuji Electric Co Ltd | トランスファ成形金型用プランジャ及びトランスファ成形装置 |
US5240939A (en) * | 1991-10-31 | 1993-08-31 | Anaquest, Inc. | Nitrogen bridge tetrahydroisoquinolines |
EA002224B1 (ru) * | 1997-03-25 | 2002-02-28 | Глаксо Груп Лимитед | Замещенные изохинолины в качестве нервно-мышечных блокаторов ультракраткосрочного действия |
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1998
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