HRP20171245T1 - Postupak za proizvodnju velikih razmjera monohidrata 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1h-indol dimezilata - Google Patents
Postupak za proizvodnju velikih razmjera monohidrata 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1h-indol dimezilata Download PDFInfo
- Publication number
- HRP20171245T1 HRP20171245T1 HRP20171245TT HRP20171245T HRP20171245T1 HR P20171245 T1 HRP20171245 T1 HR P20171245T1 HR P20171245T T HRP20171245T T HR P20171245TT HR P20171245 T HRP20171245 T HR P20171245T HR P20171245 T1 HRP20171245 T1 HR P20171245T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- hours
- formula
- piperazinyl
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 13
- XKDCUJBWVGDNSH-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole;methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O.CS(O)(=O)=O.C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C(=CC=CC=2)Br)C=C1CN1CCN(C)CC1 XKDCUJBWVGDNSH-UHFFFAOYSA-N 0.000 title claims 4
- 238000011031 large-scale manufacturing process Methods 0.000 title claims 2
- 238000006243 chemical reaction Methods 0.000 claims 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- LBQPYBWHUQEKBA-UHFFFAOYSA-N 5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1CN1CCN(C)CC1 LBQPYBWHUQEKBA-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- LOZVXBFXRPRECW-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.COc1ccc2n(cc(CN3CCN(C)CC3)c2c1)S(=O)(=O)c1ccccc1Br LOZVXBFXRPRECW-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- GWCYPEHWIZXYFZ-UHFFFAOYSA-N masupirdine Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C(=CC=CC=2)Br)C=C1CN1CCN(C)CC1 GWCYPEHWIZXYFZ-UHFFFAOYSA-N 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- VFPWGZNNRSQPBT-UHFFFAOYSA-N 2-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1Br VFPWGZNNRSQPBT-UHFFFAOYSA-N 0.000 claims 1
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Claims (12)
1. Postupak prikladan za proizvodnju velikih razmjera 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazi-nil)metil]-1H-indol dimesilat monohidrata iz fornule (I), koji sadrži:
[image]
Korak (i): reakcija 1-metilpiperazina iz formule 1
[image]
u prisutnosti octene kiseline i vodenog formaldehida od formule 2 na temperaturi u rasponu od 15 °C do 35 °C kroz period od 1,5 sati do 2,5 sati da se dobije Mannich dodatak;
[image]
Korak (ii): reakcija Mannich dodatak s 5-metoksiindolom iz formule 3
[image]
u prisustvu metanola na temperaturi u rasponu od 15 °C do 40 °C kroz period od 2,5 sata do 3,5 sata da se dobije 5-metoksi-3-[(4-metil-1-piperazinil) metil]-1H-indol iz formule 4;
[image]
Korak (iii): kristalizacija 5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indol iz formule 4 u toluenu zagrijavanjem otopine do 85 °C - 95 °C tijekom perioda od 1 sat, poslije čega slijedi hlađenje otopine do 10 °C - 15 °C tijekom perioda od 3 sata;
Korak (iv): rekristalizacija 5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indola od formule 4 u toluenu zagrijavanjem otopine do 95 °C - 105 °C tijekom perioda od 2 sata, poslije čega slijedi hlađenjej otopine do 10 °C -15 °C tijekom perioda od 3 sata;
Korak (v): dovođenje u reakciju gore dobivenog kristalnog 5-metokis-3-[(4-metil-1-piperazinil)metil]-1H-indola od formule 4 s 2-bromobenzensulfonil kloridom iz formule 5;
[image]
u prisutnosti tetrahidrofurana i kalij hidroksida na temperaturi u rasponu od 20 °C do 40 °C na period od 3,5 sata do 4,5 sata da se dobije 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indola iz formule 6;
[image]
Korak (vi): pretvaranje 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indola iz formule 6 u prisustnosti etanola i metansulfonske kiseline na temperaturi u rasponu od 15 °C do 35 °C na period od 18 sati do 24 sata da se dobije 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil) metil]-1H-indol dimezilata iz formule
[image]
Korak (vii): pretvaranje 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1H-indol dimezilata iz formule 7 u prisustnosti kašaste materije vodenog etanola i ugljika na temperaturi u rasponu od 75 °C do 85 °C na period od 0,5 sata - 1,5 sat da se dobije 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil- 1-piperazinil)metil]-1H-indol dimezilat monohidrata iz formule (I).
2. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je temperatura korištena u Koraku (i) 20 °C do 30 °C.
3. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je trajanje reakcije u Koraku (i) 2 sata.
4. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je temperatura korištena u Koraku (i) 20 °C do 35 °C.
5. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je trajanje reakcije u Koraku (i) 3 sata.
6. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je temperatura korištena u Koraku (v) 25 °C do 35 °C.
7. 7 Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je trajanje reakcije u Koraku (v) 4 sata.
8. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je temperatura korištena u Koraku (vi) 25 °C do 30 °C.
9. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je trajanje reakcije u Koraku (vi) 24 sata.
10. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je temperatura korištena u Koraku (vii) 75 °C do 80 °C.
11. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je trajanje reakcije u Koraku (vii) 45 minuta.
12. Postupak za koji se zaštita traži u patentnom zahtjevu 1, pri čemu je čistoća 1-[(2-bromo-fenil)sulfonil]-5-metoksi-3-[(4-metil-1- piperazinil)metil]-1H-indol dimezilat monohidrata veća od 99 %.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN5537CH2013 IN2013CH05537A (hr) | 2013-12-02 | 2014-02-20 | |
| EP14725245.6A EP3077375B1 (en) | 2013-12-02 | 2014-02-20 | Process for large scale production of 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1h-indole dimesylate monohydrate |
| PCT/IN2014/000109 WO2015083179A1 (en) | 2013-12-02 | 2014-02-20 | Process for large scale production of 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1h-indole dimesylate monohydrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171245T1 true HRP20171245T1 (hr) | 2017-10-20 |
Family
ID=54199404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171245TT HRP20171245T1 (hr) | 2013-12-02 | 2017-08-16 | Postupak za proizvodnju velikih razmjera monohidrata 1-[(2-bromofenil)sulfonil]-5-metoksi-3-[(4-metil-1-piperazinil)metil]-1h-indol dimezilata |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US9540321B2 (hr) |
| EP (1) | EP3077375B1 (hr) |
| JP (1) | JP6151453B2 (hr) |
| KR (1) | KR101808792B1 (hr) |
| CN (1) | CN105814020B (hr) |
| AP (1) | AP2016009224A0 (hr) |
| AU (1) | AU2014358682B2 (hr) |
| BR (1) | BR112016010788B1 (hr) |
| CA (1) | CA2929309C (hr) |
| CY (1) | CY1119298T1 (hr) |
| DK (1) | DK3077375T3 (hr) |
| EA (1) | EA028038B1 (hr) |
| ES (1) | ES2638856T3 (hr) |
| HK (1) | HK1226396B (hr) |
| HR (1) | HRP20171245T1 (hr) |
| HU (1) | HUE036008T2 (hr) |
| IL (1) | IL245619B (hr) |
| IN (1) | IN2013CH05537A (hr) |
| LT (1) | LT3077375T (hr) |
| ME (1) | ME02843B (hr) |
| MX (1) | MX364930B (hr) |
| NZ (1) | NZ719671A (hr) |
| PL (1) | PL3077375T3 (hr) |
| PT (1) | PT3077375T (hr) |
| RS (1) | RS56323B1 (hr) |
| SI (1) | SI3077375T1 (hr) |
| WO (1) | WO2015083179A1 (hr) |
| ZA (1) | ZA201602954B (hr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201809725TA (en) | 2016-05-18 | 2018-12-28 | Suven Life Sciences Ltd | Combination of pure 5-ht6 receptor antagonists with nmda receptor antagonist |
| MA45002B1 (fr) | 2016-05-18 | 2020-10-28 | Suven Life Sciences Ltd | Triple combinaison d'antagonistes purs du récepteurs 5-ht6, d'inhibiteurs de l'acétylcholinestérase et d'antagonistes du récepteur nmda |
| PT3484467T (pt) | 2016-05-18 | 2020-06-16 | Suven Life Sciences Ltd | Combinação de antagonistas puros do recetor 5-ht6 com inibidores de acetilcolinesterase |
| EA036235B1 (ru) * | 2016-10-03 | 2020-10-16 | Сувен Лайф Сайенсиз Лимитед | Фармацевтические композиции антагониста 5-ht6 |
| US20210346374A1 (en) * | 2016-10-03 | 2021-11-11 | Suven Life Sciences Limited | Pharmaceutical compositions of 5-ht6 receptor antagonist |
| SG11201913104QA (en) | 2017-07-03 | 2020-01-30 | Suven Life Sciences Ltd | New uses of a pure 5-ht 6 receptor antagonist |
| IL293416A (en) | 2019-12-02 | 2022-07-01 | Suven Life Sciences Ltd | Treatment of behavioral and psychological symptoms in demented patients |
| WO2021111320A1 (en) | 2019-12-02 | 2021-06-10 | Suven Life Sciences Limited | Methods for treating behavioral and psychological symptoms in patients with dementia |
| CN111233737B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN111362859B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN111362858B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2749846B1 (fr) * | 1996-06-17 | 1998-09-11 | Pf Medicament | Sel de methanesulfonate d'une arylpiperazine derivee de tryptamine et ses solvates pour usage pharmaceutique |
| PT1581492E (pt) * | 2002-11-28 | 2008-09-19 | Suven Life Sciences Ltd | Indoles n-arilsulfonil-3-substituídos possuindo afinidade de receptor de serotonina, processo para a sua preparação e composição farmacêutica contendo os mesmos |
| CN100378109C (zh) * | 2002-12-18 | 2008-04-02 | 苏文生命科学有限公司 | 具有5-羟色胺受体亲和性的四环3-取代的吲哚类化合物 |
| BRPI0713653A2 (pt) * | 2006-06-12 | 2012-10-23 | Novartis Ag | processo para a preparação de sais de n-hidróxi-3-[4-[[[2-(2-metil-1h-indol-3-il)etil]amino]metil ]fenil]-2e-2propenamida |
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2014
- 2014-02-20 JP JP2016535680A patent/JP6151453B2/ja active Active
- 2014-02-20 AU AU2014358682A patent/AU2014358682B2/en active Active
- 2014-02-20 PL PL14725245T patent/PL3077375T3/pl unknown
- 2014-02-20 IN IN5537CH2013 patent/IN2013CH05537A/en unknown
- 2014-02-20 KR KR1020167013965A patent/KR101808792B1/ko active IP Right Grant
- 2014-02-20 EP EP14725245.6A patent/EP3077375B1/en active Active
- 2014-02-20 PT PT147252456T patent/PT3077375T/pt unknown
- 2014-02-20 SI SI201430348T patent/SI3077375T1/sl unknown
- 2014-02-20 HU HUE14725245A patent/HUE036008T2/hu unknown
- 2014-02-20 US US15/100,489 patent/US9540321B2/en active Active
- 2014-02-20 CA CA2929309A patent/CA2929309C/en active Active
- 2014-02-20 EA EA201691161A patent/EA028038B1/ru unknown
- 2014-02-20 DK DK14725245.6T patent/DK3077375T3/en active
- 2014-02-20 ES ES14725245.6T patent/ES2638856T3/es active Active
- 2014-02-20 WO PCT/IN2014/000109 patent/WO2015083179A1/en active Application Filing
- 2014-02-20 BR BR112016010788-8A patent/BR112016010788B1/pt active IP Right Grant
- 2014-02-20 CN CN201480065601.9A patent/CN105814020B/zh active Active
- 2014-02-20 AP AP2016009224A patent/AP2016009224A0/en unknown
- 2014-02-20 ME MEP-2017-193A patent/ME02843B/me unknown
- 2014-02-20 RS RS20170853A patent/RS56323B1/sr unknown
- 2014-02-20 LT LTEP14725245.6T patent/LT3077375T/lt unknown
- 2014-02-20 NZ NZ719671A patent/NZ719671A/en unknown
- 2014-02-20 MX MX2016006629A patent/MX364930B/es active IP Right Grant
-
2016
- 2016-05-03 ZA ZA2016/02954A patent/ZA201602954B/en unknown
- 2016-05-11 IL IL245619A patent/IL245619B/en active IP Right Grant
- 2016-12-23 HK HK16114655A patent/HK1226396B/zh unknown
-
2017
- 2017-08-16 HR HRP20171245TT patent/HRP20171245T1/hr unknown
- 2017-08-28 CY CY20171100904T patent/CY1119298T1/el unknown
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