CN111247127B - 用于合成药物的中间体化合物的生产方法 - Google Patents
用于合成药物的中间体化合物的生产方法 Download PDFInfo
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- CN111247127B CN111247127B CN201880067548.4A CN201880067548A CN111247127B CN 111247127 B CN111247127 B CN 111247127B CN 201880067548 A CN201880067548 A CN 201880067548A CN 111247127 B CN111247127 B CN 111247127B
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- chemical formula
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 230000015572 biosynthetic process Effects 0.000 title description 9
- 238000003786 synthesis reaction Methods 0.000 title description 9
- 239000003814 drug Substances 0.000 title description 2
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000007810 chemical reaction solvent Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000006242 amine protecting group Chemical group 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 abstract description 5
- 229940125708 antidiabetic agent Drugs 0.000 abstract description 5
- 125000006244 carboxylic acid protecting group Chemical group 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 abstract 1
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 description 8
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- NYFSYIFADKELCR-VIFPVBQESA-N (3s)-4-(5,5-difluoro-2-oxopiperidin-1-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CC(O)=O)CN1CC(F)(F)CCC1=O NYFSYIFADKELCR-VIFPVBQESA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- -1 sulfuric acid) Chemical class 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- GAGZNRUIVHZKQV-UHFFFAOYSA-N 5,5-difluoropiperidin-2-one Chemical compound FC1(F)CCC(=O)NC1 GAGZNRUIVHZKQV-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229940125395 oral insulin Drugs 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/04—Methanol
-
- 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
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/45—Non condensed piperidines, e.g. piperocaine having oxo groups directly attached to the heterocyclic ring, e.g. cycloheximide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/12—Saturated polycyclic compounds
- C07C61/125—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system
- C07C61/13—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2017-0153334 | 2017-11-16 | ||
| KR20170153334 | 2017-11-16 | ||
| PCT/KR2018/012575 WO2019098551A1 (ko) | 2017-11-16 | 2018-10-23 | 의약품 합성용 중간체 화합물의 제조 방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111247127A CN111247127A (zh) | 2020-06-05 |
| CN111247127B true CN111247127B (zh) | 2024-02-06 |
Family
ID=66680122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880067548.4A Active CN111247127B (zh) | 2017-11-16 | 2018-10-23 | 用于合成药物的中间体化合物的生产方法 |
Country Status (8)
| Country | Link |
|---|---|
| KR (1) | KR102184129B1 (ko) |
| CN (1) | CN111247127B (ko) |
| BR (1) | BR112020009568A2 (ko) |
| CL (1) | CL2020001285A1 (ko) |
| CO (1) | CO2020006788A2 (ko) |
| PE (1) | PE20210839A1 (ko) |
| PH (1) | PH12020550635A1 (ko) |
| RU (1) | RU2741389C1 (ko) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04316526A (ja) * | 1991-04-15 | 1992-11-06 | Asahi Chem Ind Co Ltd | カルボン酸エステルのアルカリ加水分解法 |
| CN101151265A (zh) * | 2005-04-01 | 2008-03-26 | 株式会社Lg生命科学 | 二肽基肽酶-ⅳ抑制化合物，其制备方法，以及含有该化合物作为活性剂的药物组合物 |
| CN101903386A (zh) * | 2007-12-21 | 2010-12-01 | 株式会社Lg生命科学 | 抑制二肽基肽酶-ⅳ的化合物、其制备方法以及含所述化合物作为活性剂的药物组合物 |
| CN103080088A (zh) * | 2010-09-03 | 2013-05-01 | 株式会社Lg生命科学 | 用于合成药物的中间体化合物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2721185A1 (de) * | 1977-05-11 | 1978-11-16 | Bayer Ag | Verfahren zur herstellung von substituierten vinylcyclopropancarbonsaeurebenzylestern |
| TW460452B (en) * | 1998-09-14 | 2001-10-21 | Rhodia Fiber & Amp Resin Inter | Process for the crystallization of carboxylic acid and process for manufacturing crystalline carboxylic acid |
| JP2008201719A (ja) * | 2007-02-20 | 2008-09-04 | Nippon Oil Corp | テトラカルボン酸およびその酸二無水物の製造方法 |
-
2018
- 2018-10-23 CN CN201880067548.4A patent/CN111247127B/zh active Active
- 2018-10-23 PE PE2020000586A patent/PE20210839A1/es unknown
- 2018-10-23 BR BR112020009568-0A patent/BR112020009568A2/pt unknown
- 2018-10-23 RU RU2020114746A patent/RU2741389C1/ru active
- 2018-10-23 KR KR1020180126663A patent/KR102184129B1/ko active IP Right Grant
-
2020
- 2020-05-15 PH PH12020550635A patent/PH12020550635A1/en unknown
- 2020-05-15 CL CL2020001285A patent/CL2020001285A1/es unknown
- 2020-05-29 CO CONC2020/0006788A patent/CO2020006788A2/es unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04316526A (ja) * | 1991-04-15 | 1992-11-06 | Asahi Chem Ind Co Ltd | カルボン酸エステルのアルカリ加水分解法 |
| CN101151265A (zh) * | 2005-04-01 | 2008-03-26 | 株式会社Lg生命科学 | 二肽基肽酶-ⅳ抑制化合物，其制备方法，以及含有该化合物作为活性剂的药物组合物 |
| CN101903386A (zh) * | 2007-12-21 | 2010-12-01 | 株式会社Lg生命科学 | 抑制二肽基肽酶-ⅳ的化合物、其制备方法以及含所述化合物作为活性剂的药物组合物 |
| CN103080088A (zh) * | 2010-09-03 | 2013-05-01 | 株式会社Lg生命科学 | 用于合成药物的中间体化合物的制备方法 |
Non-Patent Citations (2)
| Title |
|---|
| 张澄清编著.氢氧化锂.《润滑脂生产》.北京：中国石化出版社,2007,第50页. * |
| 杨光富主编.羧基的保护.《有机合成》.上海：华东理工大学出版社,2010,第118-121页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2741389C1 (ru) | 2021-01-25 |
| KR102184129B1 (ko) | 2020-11-27 |
| CN111247127A (zh) | 2020-06-05 |
| CL2020001285A1 (es) | 2020-10-23 |
| BR112020009568A2 (pt) | 2021-03-09 |
| KR20190056296A (ko) | 2019-05-24 |
| PH12020550635A1 (en) | 2021-02-22 |
| PE20210839A1 (es) | 2021-05-06 |
| CO2020006788A2 (es) | 2020-06-09 |
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